


Heartbreaker

by notmeagain



Category: How to Get Away with Murder
Genre: Alternate Universe, F/M, Heartbreaker AU, M/M
Language: English
Status: Completed
Published: 2016-10-07
Updated: 2018-01-06
Packaged: 2018-08-20 01:33:37
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 8
Words: 24,250
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8231527
Author URL: https://archiveofourown.org/users/notmeagain/pseuds/notmeagain
Summary: Connor Walsh is a professional couples breaker. He makes his targets fall in love with him in order for them to realize that they deserve better than their current relationship. He's the best at what he does because he doesn't get involved. It's all business until he meets his next target: Oliver Hampton. Follow Connor as he and his team (Michaela and Asher) make Oliver fall in love. Inspired by the french film L'ARNACOEUR or Heartbreaker (in english)





	1. Day 0

**Author's Note:**

> it's my first time writing for this fandom. I hope this doesn't suck!

**Summary for the Chapter:**

> The beginning.

Connor Walsh is smart, clever, and extremely pretty. These are all special skills he needs in order to be excellent at what he does. And he’s the very best at what he does. He’s a professional couple breaker. Connor is perfect for the job not just because of his special set of skills but also his completely and total emotional detachment to anything. Connor doesn’t do romance, he doesn’t do serious relationships, and he most certainly does not do boyfriends.

“Being pretty is not a skill Connor,” he hears Michaela say in his earpiece.

He smirks as he surveys the busy street for his next target.

“Being pretty is  _so_  a skill Michaela. A skill you don’t have but a skill nonetheless,” Conner says and he could almost feel the glare she’s giving him through the screen where she’s watching with Asher in a flower van conveniently placed down the street and follows him around just in case something went wrong. Nothing ever did.

Before Asher could say something stupid Connor spots their target; tall, blond, and okay maybe he shouldn’t say this but  _very gullible._  Michaela insists on calling them hopeless romantics like most of his targets.

His name is Steven and his father (their client) wants Steven to break up with his no-good cheater boyfriend (they only agree to a job as long as the people are truly unhappy in their relationship but are too naive to break it off). Now, Steven would never listen to his father so that is where Connor and his team come in. They set up the scene; a meet-cute with the target, Connor charms his way not into their pants (he’s here to open their eyes not their legs) but into their heart, make them believe that this is fate instead of just a ploy to get them to break up with their horrible partners. It’s all pretty routine if you could believe it and Steven was no exception.

It went down like this:

Connor 'accidentally' bumped into Steven as he left the coffee shop spilling coffee on them both. He shyly looked at Steven and stuttered out an apology like the pro that he is. Steven took kindly,  _very_  kindly to his practiced apology and falls for his polished charm.

“So, what do you do, Jonathan?” Steven asked sweetly

“It’s really... Uh... Hard to explain,” Connor replied smiling a bit “How about I show you?”

There was a twinkle in Connor’s eyes that he knew for sure would make Steven fall for him. And Steven did. They all do.

That was how they ended up at sunset trading stories Steven tells him about his life and Connor tells him about Jonathan’s fake back story. A back story carefully handcrafted to suit Steven’s likes and dislikes. Jonathan was an art curator (because Steven loved art) that works part time teaching children how to paint (because Steven loved giving back and adored children), loves long walks on the beach (because Steven likes beaches), has a lot of nieces and nephews, and wants a big family (because Steven also wants to have a big family). Jonathan was basically perfect for Steven and that was why this next part was always so heartbreaking. For his target not for Connor. Never for Connor.

Steven and Connor who the former knows as Jonathan end up at the art museum by a big glass pane window at sunset.

“So, this is what you do?” Steven asked with a little wonder in his voice “It’s amazing.”

“Yeah...” he said then just as practiced he looks shyly at Steven “But there are something even more amazing.” It was cheesy Connor knows this but Steven blushed slightly nonetheless and smiled at him.

Steven stepped closer to Connor and Connor did the same. Steven was about to go for a kiss and Connor lets him; he always lets the target make the first move. It’s a passionate kiss (just like it always is) with tongue and sometimes biting. As always it’s Connor who pulls away.

“I’m sorry,” Steven said flustered and embarrassed “I don’t know what came over me.”

Connor smirked slightly,  _I do_ , he thought

“What are you apologizing for?” Connor asked gazing and really he’s  _gazing_  into the other man’s eyes because he’s a damn good actor “Kissing me?”

Stephen tries to look away but he can’t because Connor is looking at him like  _that_ and no one has ever resisted it. Poor Stephen never stood a chance.

“You woke me up, Steven,” Connor continued “I have never felt that alive in so long and it’s all thanks to you.”

Then Connor smiled at him. Stephen then tried to go for another kiss (just like they always do after he’s said those words) but this time he stops him.

“What’s wrong?” Steven asked looking concerned and trying to mask his insecurity.

Connor looked away running a hand through his hair.

“It’s too late for me,” Connor said sincerely.

“What do you mean?”  Steven gave him a searching look.

Connor took a deep breath and confesses Jonathan’s ‘secret’ plucking at Steven’s heart strings. He talks about divorce and depression. The usual spiel. Of course Steven bought it. He even gets teary eyed.

“The  _tears_  Connor,” Michaela reminded him and he really wanted to roll his eyes. Like he could forget about the tears.

“Yeah C-dog, you already got Stevie boy lapping it up. Take it home bro!” encouraged Asher.

Ignoring the voices in his earpiece and concentrating on his Oscar worthy performance he brings it home.

“I don’t think I can love anymore,” Connor’s voice breaks a little and when he looked back at Steven his eyes are shining “But you... you... you deserve the best.”

Steven looked at him for a moment and smiles “Thank you, Jonathan.”

“For what?” Connor asked parting his lips a little for what’s to come next.

Steven smiled wider “Just. Thanks. Thank you.” Then Steven kisses him again for the last time.

It ends like that. It always end like that.

Connor Walsh is very good at his job.

+

Connor ends up in Annalise Keating’s house. The house itself was big and daunting though not as daunting as Annalise herself.

She is looking at Connor and it feels like she’s trying to decide where to hide his body if ever he chooses to cross her.

“So,” Connor starts “What am I doing here exactly?”

“Mr. Walsh,” Annalise says “I am in need of your services.”

“I heard,” Connor says slightly wary. Annalise scares him, like a lot.

Annalise takes out a file and opens it, showing Connor the contents.

“Your next target is Oliver Hampton,” Annalise says “Step-son of a florist—”

“But they aren’t rich because of flowers if you know what I mean. He’s 30 years old, half-Filipino, 6 feet tall, graduated MIT with honors, and has a not so good relationship with his step-mom, the leader of the ‘flower business’. He’s pretty nerdy. He likes boring British dramas and video games and he hates being lied to,” Connor says he doesn’t get into the habit of interrupting Annalise but he doesn’t want to listen to facts he already knows.

“You’ve done your research,” Annalise says slightly impressed she moves on to another file “This is his fiancé Jack.”

Connor looks at the picture in the file. Jack, looks handsome enough, tall, sharp features, strong jaw, and an amazing body if the biceps are anything to go by.

“You have 10 days to break them up,” Annalise says resolutely.

That surprises Connor, usually clients give him at least one month notice before the break up actually needs to take place because there is some serious planning to be done before he and his team could execute their plan smoothly.

“Can’t do it,” Connor says “That’s too short. I need more time.”

“That’s impossible,” Annalise says

“Why?”

“They get married in 10 days.”

+

Before he and his team accept any job they research on the couple first. The research is extensive and very thorough. It includes going through garbage, spying on them individually and following them on dates. Once they do that and gather their information they go through it all with a fine tooth comb.

“This stinks,” Michaela grumbles.

“It’s garbage,” Asher points out helpfully.

“Not that I meant the mission.”

“Not the spy job of your dreams, babe?” Asher teases waggling is eyebrows.

Michaela just replies with an “Ugh.”

“So, what’d you find?” Connor asks keeping a safe distance away from the garbage as he looks at their bank statements.

“Well, if you bothered getting your hands dirty,” Michaela snaps “, you’d find out that they send each other scented love letters. Can you believe that? After three years they still send love notes.”

Asher snorts “Losers.” As he looks at the couple’s public profiles.

“Let’s dig more into it,” Connor says.

“I’m serious,” Michaela continues “I’ve never seen anyone so much in love like this. Yesterday when we were spying on them Oliver left for work and Jack followed him and said ‘you forgot something’ then gave him a kiss.”

“Yikes,” Asher says “Clingy much?”

“What are Jack’s flaws?” Connor asks.

“From what I’ve gathered he’s from a rich London banking family,” Asher reads from his laptop “He graduated top of his class from Oxford at 26. He leaves London to do charity work in Asia. Back in London, he combines his hobby and his work and starts a food bank that feeds 10 million worldwide. He's also a chef.”

“I said flaws Asher,” Connor scolds.

“I’m just reading the thing bro!” Asher says holding his hands up.

“Come on there must be something there,” Connor insists.

“Just look for something, Asher,” Michaela says.

“Alright. Alright. I’m looking no need to bust my balls,” Ashes says “Oh wait I think I got something!”

“What?” Connor and Michaela asks at the same time.

“He owns a private jet,” Asher says.

Connor holds back the urge to hit Asher's head but Michaela does not.

“Ow!” Ahser complains “What was that for?!”

“We said  _flaws_ , Asher.”

“That’s a flaw! He has a jet but he doesn’t how to fly it.”

“We’re screwed,” Michaela announces.

He couldn’t agree with her more.

+

“We can’t do it,” Connor says to Annalise

“And why not?”

“Oliver is happy. I’ve never seen such a happy couple,” There’s a slight bitterness in his tone not because he’s jealous of happy couples or anything but because he doesn’t like not having a job.

“So, just because of a little bump you’re not going to take the job?” Annalise challenges.

“Oh please,” Connor says with as much confidence he has which is a lot “With good preparation no one can resist me.”

“Afraid you might get feelings, Mr. Walsh?”

“It’s not that. It’s about principle. They’re happy therefore I don’t touch it,” Connor says and both statements were true. He’s not afraid of catching feelings because he doesn’t do those sorts of things. He knows that this is just a job no matter how complicated it is or how hard his targets fall for him.

“Very well, Mr. Walsh,” Annalise says “But if you change your mind you now have 8 days.”

+

“We can’t refuse that job,” Michaela says as soon as he walks back in the office.

“Why?”

“I don’t know if you noticed this, man,” Asher says gesturing to their surroundings “But this place is a dump. And we haven’t been having that many clients and plus we’re almost broke.”

“Almost broke?” Connor asks “Since when?”

“Since we rented out the San Gabriel Basilica a month ago then we rented out that museum for that last one,” Michaela prattles on but Connor stops listening.

“What we do is art of course it’s going to be expensive,” Connor defends but he knows it’s shit.

“Art or not we need to eat so we need to get that job,” Michaela says and he really hates it when Michaela is right.

“Fine,” Connor says defeated getting out his phone to call someone.

“Who are you calling?” Asher asks.

“Annalise,” Connor says to the phone “We’ll take the job.”

“Good,” Annalise says “I’ll send you everything you need.”

+

Back in the Keating household Annalise and a mousy blonde woman are chatting.

“Was that him?” the blonde woman, Bonnie Winterbottom, Oliver’s step-mother asks.

“Yes, it was,” Annalise answers

“You better be sure about this Annalise. He needs to be discreet and most of all this needs to work.”

“When have I not taken care of it, Bonnie?” Annalise smiles at the other woman like she knew something Bonnie didn’t. That was probably true.

+

Annalise sent them the files and even booked them a flight and adjoining hotel rooms with Oliver, how sweet of her.

“So, what’s the plan C-dog?” Asher asks “M-dog?”

“We have 5 days to make Oliver fall in love with Connor,” Michaela explains “the plan is that Connor is Oliver’s body guard.”

“Then the rest is up to me,” Connor says.

“Pretty vague don’t you think?”

“It’s vague enough. It’s a different kind of case with an impossible deadline. We’ll have to improvise.”

“By we do you mean you or literally  _we_?” Asher asks

“By we I mean all of us, Asher,” Connor says “It’s easy enough. I mean I have made guys fall for me who are  _way_  more difficult than Oliver Hampton will probably be. He looks harmless.”

“You’re right,” Michaela says trying to sound confident and failing “No big deal. This is just the case that will determine if we won’t be bankrupt by next week!” by the end her voice goes shrill.

“Woah,” Asher puts a soothing hand on Michaela’s shoulder “Calm down, babe.”

“Don’t call me that,” Michaela grits through her teeth but tried to calm down nonetheless.

“Oh how hard could it be?” Asher asks “I mean if I were into dudes I’d totally fall for Connor.”

“Thanks?”

“It’s a compliment dude. Take it.”

“Okay then,” Connor sighs “Let’s make Oliver Hampton fall in love with me.”

**Notes for the Chapter:**

> *cue rock music*
> 
> anyway thanks for reading! Let me know what you think!


	2. Day 1

**Summary for the Chapter:**

> Day 1 of Plan: Make Oliver Hampton fall in love in order to break him and his fiance up

**Notes for the Chapter:**

> thank you for your feedback and kudos! :D

Day One

Connor finds Oliver Hampton leaving his car and entering an antique bookshop across the street from the Starbucks he’s in, he’s currently wearing a suit and shades inconspicuously hiding behind a newspaper.

“You all set there, Connor?” Michaela asks in his earpiece, she was across the street by the antique bookshop’s entrance, wearing a trench coat and shades, ready to strike.

“Yup,” Connor answers confidently. Oliver looks harmless enough in person as he did in his pictures. He’s got this adorkable thing going on and it works for him pretty well if Connor was being honest. Though it was nothing the professional heartbreaker couldn’t handle.

“Good luck, peoples,” Asher says inside the flower van keeping watch.

Connor smirks at that as his eyes follow Oliver inside the shop “I don’t need luck.”

“Wow. My girl’s cocky,” Asher snorts.

“Well, maybe you’d get it if you’d let me take a shot at that ass,” Connor jokes his eyes never leaving Oliver. Maybe this was a little stalker-y but he was handsome enough to be considered an _admirer_ than a stalker.

“Sorry, bro, but this ass is already taken,” Asher replies “Isn’t that right, babe?”

“Shut up, Asher,” Michaela says.

Connor sees Oliver make his way out of the bookshop with a big rectangular book wrapped in brown paper that he puts into his messenger bag strapped over his chest.

“Michaela, that’s your cue,” Asher says, suddenly all business.

Michaela moves towards Oliver and bumps into him purposely; Oliver was a nice enough guy to brush it off and gives Michaela a polite smile. He even asks if _she_ was okay when it was so clear that Michaela crashed into him. Michaela mumbles an apology and gives a shy smile then walks away quickly.

Oliver doesn’t even notice that the book was now gone from his bag and in Michaela’s trench coat.

“I got it,” Michaela says to Connor through his earpiece.

“I’m coming to you,” Connor says and meets Michaela at the end of the street.

Michaela passes by Connor and discreetly gives him the book from her coat.

“Go get him,” Michaela says encouragingly as he passes by.

“I always do,” Connor says and goes after his latest target.

+

Oliver is opening the door to his car when a mysterious man wearing a suit comes up next to him.

“Mr. Hampton,” the Connor says “I believe you lost something.” Then he produces something that looked a lot like the book he just bought from the antique bookstore wrapped in brown paper, stamped, and everything.

Suspiciously Oliver looks inside his messenger bag and lo and behold the book was not there. Cautiously he looks at the Connor again stepping back from him.

Oliver surveys Connor carefully. Connor knows exactly how he looks because he has spent months perfecting it.

He has this very smooth and confident air around him. His suit is well-tailored and fits him perfectly. He looks like a model (if he was being completely honest) which seems to make Oliver much more suspicious.

 _That’s new,_ Connor thinks noting Oliver’s still slightly narrowed gaze

“Who are you?” Oliver asks taking the book the man was holding out warily and putting it inside his bag without taking his eyes off Connor.

“I’m your new bodyguard,” Connor says with his best don’t-you-trust-me smile.

“No,” Oliver says immediately changing his confused expression to an icy one which surprises Connor in two ways. First, no one has ever turned down his advances that fast and second, he didn’t know Oliver, so very sweet looking Oliver, could be capable of that cold of a look.

“Yes,” Connor says not even slipping because he’s Connor fucking Walsh and it takes more than a little surprise to throw him off his game “Your step-mother sent me.” Connor even added a charming smile at the end.

“Okay,” Oliver says and Connor notes a little bit of nervousness in the other man’s tone “No offense but you seem a little...” Oliver smiles at him kindly “A little frail to be anyone’s bodyguard.”

Connor raises an eyebrow at his target. His research never said anything about Oliver being a smartass.

“Built is not how you measure efficiency, sir, I assure you I am plenty capable,” Connor says a puffing out his chest a little hoping Oliver doesn’t notice but by the small chuckle Oliver tried to hide behind a cough he did.

“Ouch. Looks like little Oliver has some claws,” Asher comments and he could hear Michaela laughing. Connor tried not to grit his teeth.

“You could call Ms. Winterbottom. I’m sure she would clear things up,” Connor says maintaining his cool exterior.

“I’ll just do exactly that,” Oliver took out his phone and called Bonnie Winterbottom immediately.

+

“What is this, Annalise?” Bonnie asks inside Annalise’s office “Oliver is calling me. Your guy’s cover has already been blown.”

“Just answer it, Bonnie,” Annalise says with an eye roll “Make sure it’s actually him.”

Bonnie accepts the call and puts it on speaker.

“What’s going on here?” Oliver asks clearly upset and confused “There’s some guy saying you hired him to be my bodyguard.”

“What does he look like?” Bonnie says

“What?” Oliver’s tone is surprise and his reply is flustered “He’s... Well, he looks... Ah—hmm..Brown hair, kind of long? Um, 25 I guess and about 5ft 10.”

“Ask if he’s handsome,” Annalise says quietly enough so Oliver doesn’t hear through the phone.

“Is he handsome?” Bonnie asks

Oliver answers with a stuttered yes.

Annalise smiles “Yeah, that’s him.”

+

Oliver has been stuttering out a description of the handsome man in front of him without said handsome man, who apparently was his _bodyguard_ , noticing how hard Oliver is trying not to outright describe him as the greek god who part times as a male model that Oliver thinks he is. And by the confident yet slightly amused smirk on the man’s lips it would seem that his bodyguard sees right through him. Well, Oliver has never been one to hide his feelings well.

Through his stuttering Oliver somehow remembered that he was outraged “That’s beside the point, Bonnie! I don’t need a bodyguard I’m not 15 anymore!” he almost screamed through the phone.

“Just put him on the phone, Oliver. Please,” Bonnie says calmly like the undecipherable person that she is.

Oliver gives Connor the phone with an irritated look.

Connor just smirks and puts the phone in his left ear, the one without the ear piece.

“Yes?” Connor asks

“A bodyguard? Really?” replies a very unimpressed Bonnie

“You better hope this works Mr. Walsh,” Annalise says.

“Of course,” Connor says with assurance “You hired the best didn’t you?”

“Put Oliver back on the phone,” Bonnie instructs and he follows dutifully.

Oliver puts the phone by his ear still giving Connor a wary look.

“Listen Oliver, I have received threats and until you’re married you are still under my protection. That is not negotiable,” Bonnie says more like dictates

“Fine,” Oliver says reluctantly then hangs up abruptly shoving his phone back in his pocket.

Oliver sighs and looks at his bodyguard again “What’s your name?”

Connor isn’t sure what made him do it. He blames the sincere look on Oliver’s face again one more thing his research didn’t prepare him for, the name he blurts out is “Connor.”

“Connor!” he hears Asher and Michaela scold him through his earpiece loudly enough that made his eye twitch, good thing he was wearing sunglasses.

Oliver gives him a forced smile “Okay, then.”

+

Oliver and Connor end up in Oliver’s car with Oliver driving them both to the hotel. Connor lost the voices in his head, Michalea and Asher, 10 minutes ago because they were going to set up the bugs and cameras in Oliver’s room for extra researching purposes and set up their base too.

“So, I’ll give you a deal,” Oliver says suddenly after 15 minutes of silence “Whatever Bonnie is paying you, no matter how much I’ll double it. All you have to do is leave me alone. I promise I won’t tell Bonnie.”

Connor had half a mind to say that it wasn’t Bonnie he was afraid of but Annalise because Annalise was balls out terrifying as Asher puts it.

“Sorry. Can’t. Bodyguard code of ethics,” Connor says taking his shades off

“There’s no such thing.”

“Yes, there is. I took an oath and everything.”

“Really?” Oliver smiles at him a little mischievously and Connor is highly amused “Let’s hear it.”

“What?”

“I want to hear the bodyguard code of ethics.”

“Really?”

“Prove to me that you’re a real bona fide bodyguard.”

 _Well shit_ , Connor thought as he struggles to try and think up an oath Oliver’s face breaks into a shit-eating-grin.

“And you’re messing with me,” Connor says.

“I am,” Oliver says still smiling, eyes crinkling behind his glasses. Connor thinks he’s never seen anything as endearing.

“Seriously though,” Oliver continues “If Bonnie fears for my safety so much I can hire my own bodyguard.”

“She trusts me,” Connor says “Plus, I’m plenty capable of taking care of you.”

“Are you sure you can keep up with me?” Oliver asks somewhat jokingly.

“Please, you don’t really seem like the type to be much of a handful,” Connor says so very sure of himself.

Oliver just smiles “We’ll see about that.” Then floors it.

+

Connor has just recently found out that Oliver likes to drive fast. Also, the hotel that was supposed to be _at least_ an hour drive can be accomplished in half that if you let Oliver at the wheel.

Before Connor could even say anything Oliver gets out of the car with a smile on his face trying not to laugh at how scared Connor was for his life. Connor is _so_ going to get him back for that.

Connor follows Oliver all the way up to his room.

“This is getting creepy you know,” Oliver tells him.

“This is for your own safety,” Connor replies as he checks if the bugs Michael and Asher put were well-hidden enough.

Oliver plops down on the huge bed in the middle of the room “Are you done?” he asks the ceiling

Connor lies down right next to Oliver on the bed totally invading his personal space. Oliver turns to him, eyes widening a little and a blush rising on his cheeks.

 _This is promising,_ Connor thought smirking at Oliver.

“You’re- ah—you’re really close,” Oliver mumbles.

“I have to be I’m your _personal_ bodyguard,” Connor says almost like a purr.

Oliver sits up “Well, not that personal. I’m guessing you have your own room right?”

“I think it would be better if I stayed here don’t you?”Connor sits up as well and gives him a look “For your safety of course.” He inched closer.

“No.” Oliver gets up from the bed and paces around the room kind of fidgety “Definitely not.”

This is just perfect. If Connor had this strong an effect on him then Oliver won’t stand a chance (like everyone else).

“Are you sure?” Connor asks innocently as he lies back on the bed enticingly. Maybe Connor shouldn’t be this forward but something about Oliver getting all nervous and fidgety around him is just so hard to resist. Before Oliver could stammer out a response though his phone rang.

Oliver answered immediately obviously thankful and relieved by the disturbance. His face lights up when he saw the caller ID, it was obviously from Jack, Oliver’s fiancé.

“Hey,” Oliver says with a smile.

Connor could only hear Oliver’s side of the conversation but it was obvious how in love Oliver is with the guy and from what they’ve found Jack was just as in love with him. This is going to be a problem for them but mostly for Connor (but it’s nothing Connor couldn’t handle.)

Oliver turns his back to Connor continuing to chat with his fiancé on the phone. After 5 minutes Oliver turns a hand over the phone and says “You can leave now.” Then went back on the phone.

“Alrighty then,” Connor says kind of awkwardly and left the room only to enter the room right next to it.

+

Connor briefs Michaela and Asher about what happened with Oliver in the day.

Asher whistles “Man, you’re work is going to be cut out for you, bro.”

“You better not screw this up,” Michaela warns.

“Thanks for the vote of confidence,” Connor grumbles “Trust me. Oliver will be easy to crack I bet we even finish early.”

“If you say so,” Michaela says unconvinced.

“Whatever,” Connor huffs annoyed that she of all people would doubt his abilities. True, it’s not really their style to break a couple up who is _actually happy_ but it’s tough times for them. They needed the cash if they wanted to stay in business and this is the most fun career he’s ever had. He can make this work principles be damned.

Just before he goes to bed he knocks on the door separating his room and Oliver’s.

It takes a while for Oliver to figure out that the knocking was actually coming from inside but when he does he doesn’t at all look surprised that it was Connor on the other side.

For the second time that day Oliver manages to surprise Connor. Oliver was also ready for bed and apparently he sleeps with sweatpants and nothing else revealing a surprisingly toned body hidden by his nerd exterior. He gives Connor a blank look.

Connor gave Oliver his brightest smile “Hey, I just wanted to let you know that I’m staying right here. So, if you need anything—“

Oliver slams the door in his face.

Connor grins. _Oh this is going to be **so** much fun_


	3. Day 2

**Summary for the Chapter:**

> Day Two: The chase.

**Notes for the Chapter:**

> thanks for the kudos and comments :)

Day Two

Asher is currently briefing Connor on the latest info they gathered about Oliver after he barged in and plopped down on the bed while Michaela is off somewhere doing whatever the hell Michaela does.

“We’ve found some interesting tidbits about our lovely O,” Asher starts, showing Connor a blue folder with doodled hearts on it.

“Seriously?” Connor asks looking at the folder and taking it from Asher, sitting at the edge of the bed “and ‘O’? Who is he Oprah?”

“Just read the thing.”

“I am reading the thing,” Connor grumbled “How are these flaws? Do you not understand the meaning of the word?”

“What do you mean?” Asher asks sitting up.

Connor sighs frustrated “I mean likes jazz music, loves the king and I, his left side is more ticklish than the right,” he reads from the file “What the hell?”

“He also likes pineapple on pizza,” Asher points out

“How is that helpful?” Connor asks annoyed

Asher shrugs. “Look man, we just look for the info you’re the one who has to use it.”

“Also,” Connor goes on like Asher didn’t say anything “Who _likes_ pineapple on pizza?”

“See, that’s a flaw,” Asher points out “He’s a weird dude but there’s more,” Asher continues urging Connor to read more.

“Okay, it says here that when he was 20 he got into Julliard with a full-ride,” Connor says “Then he disappears for a year and a half without explanation then comes back and takes up computer engineering at MIT.”

Connor looks at Asher “What happened during that year and a half?”

Asher shrugs “Total mystery. No one knows. It’s like he disappears off the face of the planet for one year and six months then just comes back. Super weird.”

Connor would like to say that he was only interested in figuring out what happened during that year and a half for professional purposes but a part of him is actually, _actually,_ really intrigued by Oliver Hampton and wants to figure him out.

Just as Connor convinces himself that it’s natural to feel very curious and interested in Oliver, (it was his job after all, to feign interest, he’s just doing a really good job at it) Michaela barges in the room panting a little like she just ran which by the looks of her she probably did.

“What’s wrong?” Asher says as he stood in attention

“Oliver,” Michaela pants “He left!”

+

Connor, as he stood outside the hotel in nothing but jeans and a hastily put on black shirt, he didn’t even get to shower, was starting to get the feeling that maybe Oliver didn’t like him very much. Now, he wasn’t sure but with the door slamming in his face last night and now running away from him via getaway car... Well, he can sense a little bit of dislike there.

“Connor, he’s getting away!” Michaela screams in his earpiece while she and Asher are back in their hotel room trying to track where the hell Oliver is going.

“I know! Damn it!” Connor says as he watches Oliver in _a fucking convertible_ wearing a fedora hat, sunglasses, and a white shirt looking at Connor and driving away.

 _That little nerdy shit,_ Connor thinks. Oliver Hampton sure is full of surprises. Connor would be in complete awe of it if he isn’t so pissed that he has to chase him down now, barefoot.

“Do something!” Michaela shrieks “Follow him!”

Thinking fast Connor spots some douche in a suit talking to some other douche in a suit who, strangely, had a bike. Thanking his lucky stars, Connor promptly steals the bike much to bike douche’s protests and much to suit douche’s amusement.

“Sorry! Emergency!” Connor says quickly only a slightly bit sorry. Slightly.

He’s pedalling so fast just trying to keep up with Oliver. Oliver was driving relatively slow because he was actually almost catching up then he decides to take a left turn and Connor loses him all together.

“Where’s he going Michaela?!” Connor demands as he stops and whips his head around. He’s already at the pier whipping his head around frantically trying to see signs of one Oliver Hampton.

“The Harbour! He’s going to the pier!” Michaela shouts back at him.

“Are you sure?!” Connor asks frantically.

“Just go!” Asher says “We can’t lose him!”

“Don’t you think I _know_ that?!” Connor says harshly abandoning the bike and running towards the very crowded pier.

He separates two couples, almost runs over an old lady, and maybe knocks over a kid before he finally spots Oliver in his entire white button-up shirt, fedora hat wearing glory. He is currently getting on a boat. A boat that’s about to leave the dock.

_Shit._

+

Connor didn’t know he had it in him. He knew he was in good shape, great shape, but he did not expect himself to run all the way from the pier to the docks and then jump into a boat that was propelling away. He caught the side of it and hanged on for dear life. When he finally got in all the passengers were looking at him like he was crazy. Okay, maybe jumping into a boat was something a crazy person would do but he doesn’t really care right now.

He goes to the man wearing the fedora and white shirt who had his back against Connor. He grabs him by the shoulder to turn him around and it was not Oliver Hampton. God _fucking_ damn it.

Connor looks back at the dock where one Oliver Hampton was waving looking very amused and very guilty.

“Sorry!” Oliver shouts to him as the boat drives away further from the dock sounding much more apologetic than he should be.

Connor checks his earpiece if it’s still working “You guys still there?”

“He got away didn’t he?” Michaela asks exasperated

Connor sighs. He really didn’t want it to come to this but he has no choice.

“It’s time for plan B,” he says

+

Plan B isn’t Connor’s favourite plan but if Oliver insists on playing hard to get then he would have to use it.

Connor finds Oliver drinking coffee and typing away in his laptop looking completely engrossed by his screen, at a bistro by the pier. Connor doesn’t even try to get his attention he immediately sits across the table from Oliver and acts indignant which was easy because he’s mad as hell.

Oliver looks up startled by the sudden appearance of Connor but before Connor could get a word out Oliver is already rambling apologies.

“Look, I’m really sorry I did that,” Oliver says “I didn’t know what got into me and yeah I know that’s not an excuse you’re just doing your job and I’m _really sorry_. I don’t normally act like a jerk but that was a jerk move and you have every right to be angry. It’s just I’m really mad at Bonnie for sticking me with you so suddenly and I know that’s not your fault but I took it out on you anyway. That was my bad and—” Oliver looks at Connor in the eye takes a deep breath and sighs “What I’m trying to say is... I’m sorry.”

This takes Connor by surprise and it pisses him off how Oliver keeps coming at him from out of nowhere with not only _sincerity_ and _niceness_ but _genuine sincerity_ and _niceness_. Connor has had to deal with all kinds of targets. He had to break stubborn assholes, sweet and innocent souls (which he thought Oliver was), and all types of others, sometimes they only had one day to pull off the perfect heist but that always took at least a month of planning. Maybe if he had more research this wouldn’t feel like getting the rug pulled out from under him.

“You’re sorry?” Connor says eyeing him uncertainly.

Oliver looks back at his laptop and closes it gently “Yeah...”

“I did not expect that,” Connor says.

“What were you expecting?” Oliver asks.

“Oh... I don’t know.” Connor sighs “Maybe more snarky less sorry?”

“Oh,” Oliver says then smiles at him nervously. Things are getting awkward rapidly as Oliver fidgets in his seat and Connor just stares.

“Walsh, stop staring and say you’re line,” Michaela says in his ear and that snaps Connor right out from whatever kind of trance that was.

“Here’s the deal,” Connor says “I’ll quit and give you all the space you want I won’t even tell Bonnie. All I need is fifteen grand and I’ll be out of your hair.”

“Excuse me, _what_?” Oliver splutters “fifteen grand?”

“Well, yeah,” Connor says trying to regain some confidence he didn’t know he lost sitting up a little straighter “My services were supposed to last for five days plus breach of contract so yeah.”

Oliver looks at him for a while looking like he was having a mental debate with himself.

“Deal,” Oliver says finally and Connor should feel glad because things were _finally_ going according to plan.

Oliver brings out his check book and writes him a check for fifteen thousand dollars. He hands him the check and he takes it, folds it in half and stuffs it into his pocket.

“It was nice doing business with you, Mr. Hampton,” Connor says finally and then leaves.

Connor doesn’t go far just down the corner from the nice little bistro; he still has eyes on Oliver.

“You think he’ll buy it?” Michaela asks.

“When don’t they ever?” Connor replies.

He watches Oliver pay and leave the bistro with his laptop. Before Oliver could even get a few steps to his car someone wearing all black with a ski mask on comes running towards him forcefully bumps into him, pushing him hard onto the ground, grabs his laptop and runs.

Connor bolts. He’s running so fast trying to catch the masked man, Oliver tries to run after the guy but Connor is so much faster,  he’s beginning to think that maybe he’s done enough cardio today to last him forever.

“You stay here!” Connor orders Oliver and continues to chase after the man who had just turned a left.

Connor follows him into an alley where the masked man is waiting for him.

“Asher,” Connor says and gestures for the bag.

Asher looks at it and then to him.

“Give it, Millstone,” Connor says.

“Come on, maaaan,” Asher whines “It’s like the best laptop ever! Its specs are crazy! I could play some crazy online shit on this thing! Tell him you couldn’t get back!”

“I can’t do that because that would defeat the point in all of this,” Connor scolds

Asher takes off his ski mask and reluctantly hands him the laptop bag.

Connor turns to leave.

“You forgetting something?” Asher asks with a smirk.

Connor turns around again with a groan of protest.

“I hate this part,” Connor grumbles.

“Really? Because I love it,” Asher grins wickedly.

“Just nothing too hard that’ll leave a mark,” Connor says.

“I know prettyboy, don’t damage the goods,” Asher says then punches him the face.

+

Connor comes back to Oliver leaning on his car and fiddling with his phone. Well, more like tapping at it incessantly and less like fiddling. Oliver took one look at Connor’s face and he immediately turned concerned, every feature on his face read worried.

“Oh my god!” Oliver says “Your face.”

Connor hands Oliver the laptop bag which Oliver takes distractedly as he continues to stare at Connor’s bruised face.

“It’s just a bruise,” Connor says and tries to joke “You should have seen the other guy.”

“I don’t want to see the other guy. I want to know what the hell happened to your face. Do you know how dangerous that could have been? The guy could’ve hand a knife or a gun or something,” Oliver tells him

“I’m fine,” Connor insists. He almost feels bad at the legitimate concern of the other man. Almost. This is all just part of the play. This is all just an act.

“Are you sure?” Oliver makes a move to touch the bruise on his left cheek and he winces a little. Oliver’s touch is warm and soft and gentle and he really shouldn’t want to just hold his hand there to his cheek to make him feel better even though that didn’t make sense.

Stepping back and trapping Oliver’s hand between his own Connor says “I’m sure.”

They stare at each other for a moment both for entirely different reasons.

“Thank you,” Oliver says finally taking his hand away. Connor was a little disappointed at that.

Though he’ll never admit it.

To anyone.

Ever.

“No problem,” Connor says and really if it was almost worth getting punched in the face if he could get to see Oliver’s face like that full of gratitude.

“I think I might need a bodyguard again,” Oliver says smiling shyly.

“Yeah, I think you do,” Connor agrees smirk trying to find a place on his lips.

“You know anyone good?” Oliver asks.

Connor smiles at that, he genuinely smiles and says “I know the perfect guy.”

 

**Notes for the Chapter:**

> it's shorter than intended but oh well i tried and that's what matters... also if anyone notices the thing that I put here then good job :D


	4. Day 3

**Summary for the Chapter:**

> Day Three: Some quality time.

**Notes for the Chapter:**

> wow that was a long wait. sorry about that. I hope you like it though! Thanks for the comments and kudos ma dudes!

Day Three

Connor and Oliver are currently driving to Oliver’s --- Oliver and Jack’s --- wedding venue. The wedding is at the edge of a cliff because why not.

“It was Jack’s idea,” Oliver explains in the passenger seat. Connor insisted on driving because he will _not_ let Oliver take the wheel again.

“Sounds poetic,” Connor says “Kind of.”

“I guess so.” Oliver shrugs eyes trains on the road.

Connor catches on the tone of Oliver’s voice but he can’t really put a name on though he does note that it isn’t a positive one. He needs to take advantage of that.

“You don’t like it I’m guessing?” Connor says side-eyeing Oliver as the other man slumps further in his seat.

There’s a silence and Connor was thankful that he isn’t wearing his earpiece right now with Asher and Michaela trying to work out how to ruin the air conditioning in Oliver’s room back at the hotel because he likes to think that he works better without voices in his head.

“Not really. I mean, it’s fine I guess but I’d rather elope than to this big wedding thing which he insisted upon but didn’t even help plan,” Oliver says showing a lot of annoyance. “Plus, I mean figuratively taking the plunge by the side edge of a literal cliff? I mean it’s kind of cheesy right?”

 _This is good,_ Connor thinks, _I could exploit this._

“And you don’t need to know any of that,” Oliver says at the end probably kicking himself internally for opening up to a total stranger.

“Hey, if you can’t tell your bodyguard who can you tell?” Connor says with a smirk.

“Probably people I’ve known longer than three days.”

“Fair enough.”

They reach the wedding venue and it was actually pretty neat. There was a gazebo thing by the edge of the cliff where the groom, groom, and priest should be. There were already some posts set up ready to be decorated. It’ll look simple but elegant when it’s finished and Connor says so.

“That’s what I was going for so thanks,” Oliver says as he looks at the coming tables and chairs.

They make their way to the gazebo by the edge of the cliff; Oliver looking out to the waves and Connor looking at him.

“You planned this all by yourself?” Connor asks.

“Yes,” Oliver says curtly.

Connor smiles to himself. He’s hit a nerve. He can take advantage of that and of course he does exactly that.

“Did you go all bridezilla?” Connor teases.

Oliver sighs “I had to since Jack didn’t have time to help me plan anything.”

Connor was about to say something along the lines of _wow, how selfish of him_ or _and he just left you to do all the work?_ Or _not an ideal way to start your married life but whatever works for you._

When Oliver says “But he’s busy and far be it from me to take him away from war orphans. Plus, he feels really guilty about it and I guess it’s sort of fun getting to tell everyone around with free reign. I don’t mind really.”

Connor raises his eyebrow at him and Oliver shrugs “I don’t mind _that_ much,” he says in the end.

 _Huh,_ Connor thinks.

“So, how’d you two meet?” Connor says instead.

Oliver smiles at the memory and Connor grits his teeth a little because why does breaking up happy couples so difficult.

“We met in Paris actually,” Oliver says smiling.

“How romantic,” Connor says.

“Not really. I was lost and spoke horrible French he was hot and speaks great French. He basically saw me embarrass myself trying to look for the Louvre and decided to take pity on me,” Oliver explains.

Connor let’s his eyes drag slowly across Oliver’s form making sure Oliver knew he was checking him out. By the looks of Oliver’s blush and sudden nervousness he’s definitely noticed.

“He probably didn’t do it out of pity,” Connor says in a flirty tone.

 _A meet cute? Really?!_ Connor thinks in slight outrage. He knew getting into this that it would be difficult but he’s fighting against a fucking romantic comedy and it’s unfair. Aside from its cheesiness, Oliver and Jack’s relationship is literally the thing that Connor is against.

“You two seem very happy,” Connor says reeling back a little “Well, you seem happy with him anyway.”

“What do you mean?” Oliver asks taking the bait.

“Hm? Oh it’s nothing just... two days before the wedding and he’s not here...”

Oliver is silent. Then “He’s busy.”

“Too busy to help you out with stuff for your wedding?”

“Okay, you don’t really know anything so don’t judge,” Oliver scolds him. He’s getting angry and Connor shouldn’t enjoy this so much.

“I’m just making an observation,” Connor defends and then “I’m sorry.”

“It’s fine,” Oliver shrugs it off like the nice guy that he is. If Connor was a better person he’d feel bad for trying to play such a nice guy but he’s not so he doesn’t.

Not even a little bit.

He swears.

Oliver starts to go back to checking the chairs the delivery guys just brought up.

“Isn’t it too early to be having the chairs here?” Connor asks following Oliver

“It was either get them here early or get them here late.”

“They’re nice chairs.”

“Thank you,” Oliver smiles and Connor can’t help but smile too.

+

Connor calls Annalise.

“What is it Mr. Walsh?” Annalise answers already impatient “Has Mr. Hampton fallen in love with you yet?”

“Not yet but everything is going according to plan,” Connor lies.

“Then why are you calling?”

“I think it would go better if I got the whole story.”

“You want to know why Ms. Winterbottom doesn’t want the wedding to happen.”

“Exactly.”

“Mr. Walsh,” Bonnie says coldly from the other end of the phone “I am paying you to act not to ask questions. Got it?”

“Yep,” Connor replies.

 _Well, that went nowhere fast_ , Connor thinks miserably.

+

On their ride back Connor decides to make conversation again.

“So, how long have you and the fiancé been together?” Conner says conversationally, casual but calculated.

“Hmm?” Oliver says snapping out from his thoughts “Oh, um, about three years going on four now.”

“Long time.”

“Kind of.”

“So, what were you doing in Paris?” Conner asks “You know when you met Jack.”

“Oh, yeah the company I used to work for sent me to Paris for six months to set up a new branch there,” Oliver explains “It’s kind of funny because we kind of danced around each other for six months because he thought I moved to Paris for good and I thought he lived in Paris then suddenly a month before I have to leave he confesses his feelings to me and then it just evolved from there.”

 _Seriously?_ Connor thought as he gripped the steering wheel a little tighter than he should. _I’m up against a fucking cliché._

“Wow,” Connor said instead.

“Yeah.”

Something about the way Oliver told their story bothered Connor. If he could get Oliver talking long enough maybe he could figure out what it was and how he could turn that into his favour. He was about to say something to Oliver when he saw the other man asleep in the passenger seat.

He didn’t have it in him to interrupt the peaceful slumber. Oliver looked to peaceful.

Connor might be getting into some pretty dangerous territory he chose to ignore and drove on.

+

In the meantime, Asher and Michaela were discreetly wrecking Oliver’s hotel room.

“So, which one the air-conditioning or the sprinklers?” Asher asks thumbing the screwdriver.

“Why not both?” Michaela smiles wickedly.

“You’re so smart, babe.”

+

That evening Michaela intercepted a call from Oliver’s suit.

“Hello?” Oliver says “Yeah, my air-conditioning just turned on and I can’t get it to turn off. It’s freezing inside”

“Don’t worry sir,” Michaela responds sweetly “We’ll get a repair man to you as soon as possible.”

Asher emerges from the bathroom in a jumpsuit and a pornstace.

“What is that?” Connor asks highly amused.

“It’s my look,” Asher says all cocky “How do I look?”

“You look like a low-grade porn star,” Conner says simply.

“Shut up, Walsh. I look good in this.”

“If you say so.”

“Wish me luck,” Asher says with a wink and kiss.

Conner and Michaela turn their attention to the monitor.

They watch as Asher enters Oliver’s room as the most stereotypical plumber in the history of the world.

Asher fumbles an introduction and Oliver shakes his, they could hear everything over Asher’s earpiece.

“ _Vhat seems to be ze problem_?” Asher asks with a strange Russian, German, French accent hybrid.

“The air-conditioning is broken,” Oliver says shivering as he hugged the blanket over himself tighter.

“What is that accent?” Connor asks Michaela horrified.

“I have no idea,” Michaela replies. “What an idiot.”

“ _Zonut vorry. I am ze ixpert. I fix anything no problem._ ” Asher reassures.

Asher then goes and breaks the air-conditioning more which then triggers the sprinklers.

“Oh my god!” Oliver says as he tries to salvage his laptop from getting too wet.

“ _Pliz, no tell the manager. Pliz I hev a family. Please, not tell._ ” Asher pleads his accent getting heavier and then lighter.

Oliver looks torn and very sympathetic. It was official Oliver has a heart of gold. Asher keeps blabbering out excuses and apologies his accent varying. Connor took that as his cue.

He busts through the door of their adjoining room, all business like and professional.

“Is there a problem here?” Connor says as he looks at Oliver and Asher pretending to assess the situation.

“No,” Asher says then looks at Oliver pleadingly.

“No,” Oliver confirms with a shake of his head. A heart of gold, truly.

“It’s cold in here yeah?” Connor says.

+

Connor and Oliver were now in Connor’s room with Asher pretending to fix everything he broke in the next room he would casually shout out reassurances.

“Don’t you want me to close the door?” Connor offers as Oliver paces back and forth in front of the TV.

“Yes, please,” Oliver says as he continues to pace. “What am I going to do? I mean I can’t call in the front desk because he would be in trouble but where am I going to sleep?”

Connor’s heart would have warmed at the sight of Oliver worrying over a man who was clearly incompetent, if he still had a heart that is.

“You could sleep here,” he suggests as he plops back down on the bed in a slightly evocative pose.

Oliver stops his facing and looks at Connor with a flush on his cheeks. “Um.”

“I mean. I can sleep in the car. It’s fine, I’m used to it,” Connor clarifies and gets up to clear some of his stuff.

“No, don’t do that,” Oliver says “I mean. You can take the couch. You don’t snore right?”

Oliver gives him a small smile and Connor gives him a smile of his own that wasn’t entirely fake.

“Thanks,” Connor lifts his bag down and purposely accidentally drops a DVD of _The King and I_.

“Hey, what’s that,” Oliver inquires moving to pick up the fallen DVD.

“Ah-“ Connor quickly gets the DVD and holds it close to his chest “- Nope! Hey, um. What.”

“Come on,” Oliver says with a quiet laugh “Give it.”

Connor hesitantly, just the right amount of shy to be endearing, hands the DVD over.

“Now, there is nothing to be ashamed of. I actually love this movie.”

“You do?” Connor asks with practiced surprise which Oliver doesn’t notice at all.

“Totally,” Oliver smiles brightly and Connor blinked.

“Do you want to watch it?” Connor’s question is hinted with a genuine kind of shyness now with the onslaught of Oliver’s bright and sunny smile.

“I’d love to.”

“Great.”

“But I have one condition.”

“What?”

“Don’t make fun of me.”

“I promise.”

+

They were currently sitting at opposite ends of the couch. Oliver watches the movie and lip synchs along the songs, Connor is too busy watching Oliver to pay attention to the movie.

“You’re lip synching,” Connor points out.

Oliver grabs a pillow and throws it at him with a laugh “What did I say of making fun?”

Connor laughs too “I wasn’t!”

“Whatever you say.”

“I swear!”

Oliver still has a smile playing on his lips when he turns his attention back on the film while Connor can’t seem to take his eyes off the man on the other end of the couch.

“I love this part,” Oliver says absentmindedly.

“Me too,” he says still looking at Oliver.

+

Sometime later Oliver was sleeping on the bed with Connor on the couch. He watched Oliver sleep for moment while he thinks about all of this. The scheming, the planning, and right now in the middle of the night with no one else around he could admit to himself that yes, he felt a little guilty about breaking Oliver’s heart.  Oliver is too nice of a guy, really he is but Connor has a job to do and if his step-mother thinks this is best then who is he to argue.

He thinks about Oliver’s innocence at this moment. At every moment.

He doesn’t even know he’s being played.


	5. Day 4 pt 1

**Summary for the Chapter:**

> Day Four: The Morning of the day before the day before the day of the wedding

**Notes for the Chapter:**

> im sorry i took like a year off. my bad peeps. anyway i added one more chapter to the whole thing.

Day Four Part: 1 The Morning

Connor wakes up in the middle of the night on the couch. He tries to go back to sleep but strangely can’t. He feels restless.   He looks over at where Oliver is sleeping peacefully. His throat feels tight and not for the first time does he feel bad about this job. A job. That’s what this is. He hopes Oliver doesn’t hate him too much after all of this is over. He berates himself because why should he care whether or not Oliver hates him after this? He sighs and drops himself back on the couch eyes closed. It wouldn’t matter if Oliver hated him. After this he’d never get to see him anyway. He ignores the tightness in his chest as he struggles for sleep to come back to him.

When sleep finally took him he dreams of coke bottle glasses, sweet smiles, and a beautiful laugh.

+

 Oliver wakes him up in the morning shaking him gently from a fitful sleep. It was a nice to wake up to-- Connor’s bleary mind supplies—with Oliver smiling down on him all gentle and sweet and _nice_.  He smiles back sleepily.

“Hey,” Oliver says.

 “Hey.” Connor replies. It takes another second of Connor just staring back at Oliver when his brain kicks back in. It startles him to action and clears his head up. He sits up abruptly almost bumping heads with Oliver. “Um. You’re awake early.”

“Yeah, I got room service deliver some food so maybe you’d want some breakfast?” Oliver offers.

Oliver was sitting on a chair next to the coffee table with his laptop propped on his lap. The table was full of regular breakfast food, fruit, coffee, and juices.

“Thank you,” Connor says a little bit in a daze.

There was a silence as Oliver busies himself with his laptop and Connor occupies his time by eating breakfast and trying not to stare too openly. He needs to get a grip or at the very least get his head back into the game. They have a plan _damn it_. He will go take Oliver to the bay and then he’ll make his speech about a dead lover and how everyone should get the love they deserve. He’ll cry a little bit and because Oliver is such a bleeding heart he’ll try and comfort him. Then that’s when he’ll pounce and after that he’ll break his heart and leave him forever.

Connor tries to bury any sort of semblance of feeling that’s trying to weasel its way into the place his heart is supposed to be by taking another mouthful of croissant.

He steels himself for what he’s about to do.

The plan is already set. Nothing he can do about it now. If he’s lucky and the universe doesn’t decide to fuck with him some more this can be over with before lunch.

He takes one last bite of his croissant and sips his coffee.

“I’ll wait for you outside and accompany you for your morning run,” Connor says in his best business voice.

Oliver snickers, goddamn actually fucking, _snickers_. “Okay.”

“I’m serious.”

“Of course.”

“Oliver.”

Oliver looks up from his laptop. “Connor.”

Connor gives him a look. “I’m very concerned about your safety,” he says with all the sincerity he could muster which turns out to be a lot.

Oliver smiles at him warmly. “I know. I promise not to run off. Well, not run off without you knowing where I’m running to anyway.”

“Thank you.”

Before Connor could say something stupid he excused himself saying he’d give him some privacy so he could get ready.

“It’s your room you know,” Oliver calls out to him as rushes to the exit. “My stuff is still in the other room.”

+

Connor is greeted by Asher when he enters their makeshift headquarters which is also Asher and Michaela’s room.

“How’d it go Con-con?” Asher asks all annoyingly bright and sunny and it makes his face extra punchable.

“We turned off the cameras after you got Oliver into your bed,” Michaela says suggestively. “We didn’t want to see anything unsettling.”

“Like I was going to have sex with him,” Connor scoffs. He hates how it sounded like he was somehow out of Oliver’s league when it’s clearly the other way around. It makes his guts twist in a way it never has before. It unsettles him.

Michaela just looks at him funny and gives Asher a knowing glance.

“What?” he asks through grit teeth.

“Just get the job done, Connor,” Michaela says. “We’re under time, over budget, and going under real soon so the sooner we get this done—by we I mean _you_ \--- the sooner all of us get out of here.”

Connor lets out a long suffering sigh.

And because things could always go worse he gets a call from Annalise.

+

“Is everything going according to plan, Mr. Walsh?” Annalise taunts from the other side of the phone.

“I’m working on it,” he says.

“So, you’ve made no progress,” she states blandly.

“It’s still going,” he replies irritably.  “We’re going to go for a run to the bridge and once we’re there I’ll tell him the whole spiel and we’ll be over and one with it by the end of the day.”

“You’re time is very limited Mr Walsh,” she reminds him pointedly.

“Don’t have to tell me twice.” She really does not. He can actually feel her breathing down his neck through the phone.

“Good,” Annalise says and he could hear the evil smile spread across her face. “Good bye, Mr. Walsh.”

She hangs up on him and he’s left feeling a directionless anger. He swears she only called him to antagonize him.

Michaela and Asher look at him funny and he just glares back. He does not like the feeling of the two of them acting like they know something he doesn’t.

“Tense,” Asher mutters under his breath.

Michaela replies with a look that conveys _‘you got that right’_.

“Shut up, Asher,” Connor says and gives Michaela a look as he shuts the door to the bathroom so he can prepare for the day ahead.

+

Connor enters his room to find Oliver gone. Panic seizes Connor immediately and he rushes to their adjoining door. He opens it and is greeted by a shirtless Oliver wrestling to get a long-sleeved shirt over his head. He takes a moment to appreciate the long expanse of Oliver’s long tan back. Then Connor was greeted with a full view of Oliver’s front when he turns around still with his arms caught up in the shirt. Connor quickly looked at the strong chest down to his surprisingly defined abs. He licks his lips absentmindedly.

Oliver finally manages to get the shirt over his head and cover his wonderful torso. Connor makes a disappointed hum and clears his throat which surprises Oliver.

“Did I startle you?” Connor asks innocently loving the blush that spread over Oliver’s cheeks. He wonders if it would go all the way down to his chest.

“Uh yes?” Oliver says running a through his mussed up hair. He looks down on his shirt making sure it’s properly covering him.

Connor notices Oliver’s glasses were crooked on his face. He can’t help but tease.

“Did you try putting your shirt on with your glasses and got stuck?”

Oliver, to his delight, blushed harder. “Shut up.”

“No judgement.” Connor raises his hands non-threateningly smiling all the while. He takes a step towards Oliver getting closer until they were inches apart. Oliver just stares at him all flustered.

“It’s just you’re glasses are crooked,” he says gingerly righting Oliver’s glasses. He can’t help but brush hair a stray hair from Oliver’s face unintentionally tender.

Their eyes meet.

Oliver’s phone rings shrilly on the bed.

Oliver steps away abruptly putting as much distance between them. He quickly steps into the balcony not giving Connor another glance. Connor doesn’t know how to feel about that. So, he decides to not feel anything about it at all.

He sits on the bed and watches Oliver probably talking to his fiancé about the wedding and how much they miss each other and true love and all that other sentimental crap. He shouldn’t feel bitter about it really. He doesn’t care. He keeps telling himself that.

+

“Do you think he realizes it yet?” Michaela asks Asher as they head to the marina to set up their follow up plan in case the first plan needed a little redoubling. With the way things were going they probably needed more than a plan B.

“Personally,” he says. “I think he thinks he’s caught a cold or something. He doesn’t know what feelings are apparently.”

“You think we have a shot in hell in getting this job done as quickly and cleanly as possible?”

“Probably not,” he admits cheerfully.

“I thought so,” she says dejected.

“On the bright side Connor might be growing as a person,” he points out. “Hey, if all this goes south we still have each other right boo?”

Michaela can’t help but smile at that. Asher can be a bit of an idiot sometimes but he’s her idiot and that will never change.

“There’s still that,” she agrees as they trudge onto their assignment.

+

Connor is following Oliver dutifully on their run like a good little bodyguard.

Oliver from time to time looks behind him maybe checking if Connor was still there. Connor was sure he won’t try to bolt again because not only did they make it convincing that he needs a bodyguard watching over him but also because Oliver is just too damn nice to mess with him again.

Oliver looks behind him at Connor one more time and says, “Stop that.”

“We’ve been over this. This is my job.” Connor jogs a little closer. “I’m supposed to follow you around everywhere you go.” He gives a cheeky smirk just for good measure.

“No, I meant.” Oliver chuckles. “Stop following me and run next to me?”

Connor looks at him unsure playing up the rule abiding guard shtick.

“Please?” Oliver asks nicely. “It feels weird. I’m not a celebrity you know.”

“Alright,” Connor says. “You’ve convinced me.”

Oliver gives him a bright sunshine smile. Connor smiles back.

“Hey,” Connor says.

“Yeah?”

He’s been dying to bring this up since he saw Oliver get this strange look on his face in the balcony earlier this morning.

“So, um, you talked with Jack this morning,” he tries to sound casual. “Is he coming in today?”

Oliver shakes his head. “That wasn’t him. It’s my friends their coming in earlier than expected so they just wanted me to know.”

He glances at Oliver and he knows there something he isn’t telling him. He’s concerned of course but only because he feels like he could use this for his advantage.

“When is the fiancé coming in?”

Oliver stops running and rests his hands on his knees taking deep breathes.

Connor is instantly alarmed. He knew asking this was a risk.

“Hey! Are you okay?”

“No. No. I mean yes. Yes.” Oliver waves him off. “I’m fine. Seriously, I’m fine.”

Connor approaches him warily. “Are you sure?”

Oliver straightens up and sighs. “He won’t answer his phone.”

“Oh,” Connor says. It’s all he could in surprise.

“I’ve been calling him all morning and there’s no answer and I don’t know. He was really weird last time I talked to him too and I just. Right now, I’m just really worried because he’s not answering my messages.”

“I’m sure he’s fine,” Connor says reassuringly. He then curses himself because he shouldn’t be reassuring right now. He should play that doubt and make it bigger than it was supposed to be. He should be doing opposite of what he’s just done. But Oliver just looks so sad and he felt a little angry at the guy making Oliver feel sad. It’s ironic really.

“It’s going to be alright,” he says.

“Thanks.” Oliver smiles. “Sorry for unloading on you like that.”

“Anytime.” Connor gives him a winning smile and says, “You know if I was a lesser man I’d make a joke about you unloading one me.”

That earns him a hearty laugh that warms his bones. They start jogging ahead again.

“But you’re not a lesser man are you?” Oliver asks all crinkly eyed and smiling.

“I’m a professional,” he replies solemnly cracking a smile as well.

They run in companionable silence for a little while following the path.

“I’ll check the perimeter,” Connor says running ahead leaving a confused Oliver following him.

Connor leads them to a place familiar to Oliver and pretend-familiar to Connor. The path opens to a bridge overseeing the ocean. A lot of people were milling around them other joggers and just some locals doing their thing.

He runs to the edge of the bridge looking for the ‘x’ that marks his position on the railing. He stops at his mark and covers it with his hand.

“You’ve checked the perimeter?” Oliver asks out of breath. Connor appreciates that for once he’s the one winded.

“All clear.” He turns to Oliver who is looking appreciatively at their surroundings. Just like they knew he would. It was a similar place Oliver’s mother would take him when he was young. It was Michaela’s idea to lead Oliver hear so Connor could execute his speech and tug at his target’s heartstrings.

Connor’s brain goes on auto-pilot. He’s done this a hundred times before. He knows the speech by heart. He knows when to look into his target’s eyes, he knows when to make his voice crack from emotion, he knows when to makes his eyes water brimming with unshed tears, and most of all he knows how to act like he’s heartbroken even though he’s never been that.

He watches as Oliver’s face turn from confusion to concern to sympathetic. He gets to the part about his imaginary lover. He talks on and on about their non-existent relationship and how his heart broke. Finally, he looks at Oliver intently with almost tears in his eyes and his voice might be shaking a little.

He goes in for the kill relaying the lies he’s memorised and executed perfectly before. It gets the desired effect. He’s a little upset that Oliver can’t see through it. That Oliver doesn’t call him out. He wants him to.

Before Connor can say the last line that will really hammer the last nail into the coffin Oliver does something unexpected. At this point Connor should have seen this coming a mile away. But he doesn’t. And he’s left scrambling. Oliver hugs him.

Oliver hugs him pulling him close and safe. Connor doesn’t know what else to do but hug him back. He rests his head on his shoulder and he appreciates how tall Oliver is.

“I’m sorry,” Oliver murmurs on top of his head.

Connor just holds him closer.

The moment either lasts forever or five seconds before Oliver’s phone pings with a reminder and their embrace is over.

“Let’s go back,” Oliver says starting to jog away. “I have an appointment.”

Connor follows.

+

On their way back Oliver is chattier. Connor is still reeling.

“You snore by the way,” Oliver says.

“So do you,” Connor replies.

They look at each other and smile.

If it was possible to be killed by kindness he’d swear to god he’d probably already be dead by now. It’s okay. He’s a horrible person anyway.

**Notes for the Chapter:**

> thanks for staying with me


	6. Day 4 pt 2

**Summary for the Chapter:**

> Day Four Part 2: More scheming

**Notes for the Chapter:**

> what is this? another update? in the same month? shocking. I'm trying to just get everything done before my vacation is over so here you go. happy holidays. thanks for sticking with me! we're almost there folks!

Day Four Part 2: Afternoon and Evening

On their run back to the hotel Oliver informs him that the friend is coming over to the appointment has a surprise for him later in the evening effectively ruining his team’s original plan. He runs ahead of Oliver using the excuse of checking the perimeter again. Oliver gives him a confused look but shrugs it off and lets him run ahead.

Connor is on the phone with Michaela telling her about the new development. Oliver was entranced by a little niche store on their run back and insisted he needed to take a look around.

“We have to cancel the marina,” Connor says. “Apparently, Oliver has friends coming in to spend the evening with him.”

“Shame,” Michaela says. “We taught the dolphins your names.”

“Try to find out what the friend is planning maybe we can do something with it.”

“Already on it big-C!” Asher yells through the phones.

“I’ll keep you guys posted.”

 “Goodie,” Michaela says with nothing but pure sarcasm.

“Do you have any intel on the friend though?”

“As far as we know they’ve been friends for years. There’s no trace of how they met or when but according to our research they met exactly around time Oliver disappeared.”

“Great,” Connor muttered. “Just what we need another rogue element.”

“This job is just chock full of surprises,” Asher says.

“Don’t make it sound like that’s such a good thing, Asher,” Michaela scolds.

“Well, sorry for finding a little excitement in our life.”

“Our life is plenty exciting enough.”

“That’s so sweet of you to say, babe.”

“Okay, I’m hanging up now,” Connor says pocketing his phone. Those two really gets on his nerves sometimes.

+

Oliver meets his friend at the caterers to try the final additions to the menu which were some extra desserts and cocktails.

“I know I’m biased right now because there’s another human being growing inside of me, but everything is delicious,” Oliver’s severely pregnant friend, Laurel says. “God, I wish I could try those cocktails.”

“Please, don’t try the cocktails,” Oliver says with a chuckle. “Think of the baby.”

“Oh, please I’ve been thinking about the baby for 9 months!” Laurel says.

“I think I can ask them to make a Shirley Temple?” Oliver offers because he’s nice. “It’s non-alcoholic but you know better than nothing.”

Laurel makes a hum of agreement as she scoffs down another cake. Connor looks at her and wonders how big the baby will actually be when it’s born and how she was able to fly in when she’s clearly ready to go into labor any moment.

She notices Connor eyeing her and says, “Don’t judge me I’m pregnant. Ollie, tell your creepy bodyguard to stop standing there and judging me.”

“Connor probably isn’t judging you,” Oliver says obviously finding her antics amusing. “Although I have told you before stop being creepy and sit down.”

“I definitely wasn’t,” Connor assures her but doesn’t sit.

“Uh huh,” she tells Connor then turns her attention to Oliver. “What’s the deal with that guy?”

“I’m right here,” he points out.

“What do you mean?” Oliver asks.

“Why do you need a bodyguard?”

Oliver shrugs. “It’s a long story I’d rather not think about.”

“He’s kind of cute in a pretty sort of way,” she says matter-of-factly. “Although he looks more like a model than a bodyguard though.”

“He does! Doesn’t he? That’s exactly what I told him!”

“Again, I can hear you. And I have proven myself plenty capable!”

“Really?” Laurel raises a brow. “Ollie, has he proven himself ‘plenty capable’?”

“Oh sure,” Oliver says. “He got punched in the face for me the other day.”

“See, now a good bodyguard wouldn’t have gotten his face punched in the first place.”

“Well, now that you put it that way,” Oliver says while trying not to laugh.

“I am a good bodyguard,” Connor says a little awkwardly but solidly as he tries to prove himself.

“Sure, you are sweetie,” Laurel says in her most condescending tone.

“Come on, Laurel,” Oliver says certainly giggling now. “Stop harassing my bodyguard. He’s been nothing but nice to me.”

“Whatever you say, Ollie,” she says innocently as she takes another bite of her cake slice.

Connor can’t believe he’s being bullied by a pregnant lady, but he supposes it’s alright since it seems Oliver is having a good time although he still feels like a vein is going to pop. Oliver gives him an apologetic smile. He smiles back a little already feeling better.

Laurel excused herself to the ladies’ room some time later because she was very pregnant and really needed to pee.

After Laurel left Oliver couldn’t take Connor just standing there by their table any longer and insists for him to sit. Olive pulls Connor by the hand and makes him sit on the seat next to him. Connor let the linger for far too long and thoroughly enjoying the way Oliver blushed when he realized what was going on.

Before Connor could say or do anything Oliver gives him a shy smile.

“Sorry about Laurel,” Oliver says giving him a sweet apologetic look.

“What’s there to be sorry for?” Connor jokes.

“I know, I know,” Oliver laughs. “It’s just she doesn’t like personal security all that much.”

“It’s fine,” he assures.

Oliver smiles and Connor returns it. He then looks directly at Oliver knowing it would make him squirm.

“What?” Oliver says finally a hint of blush dusting his cheeks.

“You have a little---” Connor gestures to his face. “--- chocolate sauce smeared here.”  Even when there isn’t.

“Oh!” Oliver picks up a napkin to wipe it off, but Connor stops him.

“Here,” Connor says taking the napkin from Oliver’s hand gently. “Let me.”

“Uh, sure,” Oliver mumbles as Connor slowly wipes the corner of Oliver’s mouth. He doesn’t know quite how to play this yet. Should he go for the innocently bashful trying to keep his eyes from staring too long at Oliver’s mouth only to realize staring at his eyes would be worse. Should he go for intensely sensual and look into Oliver’s eyes as he wiped his lips. Should he concentrate dutiful on Oliver’s lips and then be surprisingly taken aback by how suddenly close they were and look deeply into his eyes as if seeing them for the first time. All good tactics but he needs to choose one.

Before he can enact his master seduction Laurel comes back.

“Oliver!” Laurel says going to the table. “I can’t believe it!”

Oliver quickly jumps as far away from Connor as the space would allow and Connor is left in an awkward daze.

“The bathrooms here are incredible!” Laurel says excitedly as she took her seat.

“Oh, uh, really?”

Laurel smiles and they continue on with their tasting while Connor sits there mildly miffed. He’s pretty sure he should be mad that his plan got foiled but he’s also pretty disappointed that he didn’t get to see Oliver blush harder.

As they were leaving Laurel swoops in right in between Connor and Oliver. She wraps her arm around Oliver’s and pulls him to the exit chatting away about everything that’s been happening to her. Connor follow them from a respectable distance. Before they can exit the restaurant Laurel looks directly at him and glares knowingly.

 _Shit,_ Connor thought. _She might be onto me._

+

Back at the hotel room Connor, Asher, and Michaela were setting up the plan for tonight.

“What are we doing?” Connor asks. “You find out what their plans are?”

“Laurel is going to surprise Oliver with theatre tickets. They’re going to a play,” Michaela says. “So, that means you’re going to a play.”

Connor groaned in misery.

“It’s a musical actually,” Asher clarified clearly enjoying Connor’s torture.

“So, what do I have to do?” Connor asks. “Be a part of the musical? Sing?”

“God, no!” Michaela says remembering Connor’s singing.

“You’re dreaming too big Con-con,” Asher says. “No, you’re just going to have to watch it like the rest of the pleabs.”

“That’s it?”

“Of course, that’s not it.” Michaela hands him a thick stack of paper. “Read this.”

“What is this?”

“That’s the entire script of the musical with the songs and everything,” Michaela says simply. “You read it, you memorize it, you mouth all the words to the play and sing a long quietly to all the songs and you’ll be golden.”

“And where will they be while I’m doing all this?”

“They’ll be at the box seat with the perfect view of you in the middle.”

Connor looks at the stack of papers he’s been handed and starts riffling through them. He resigns himself to the horrible task ahead of him.

+

Connor calls Oliver early in the evening.

“Hey, Connor,” Oliver answers. “What’s up?”

“Hi, Oliver, I know it’s a bit sudden, but can I take the night off?” Connor, Asher, and Michaela were all watching Oliver as he prepared for tonight’s show over the camera they installed in his room.

“Uh, sure. No problem.” Oliver is trying to tie his bow tie but is failing miserably. Connor hates how he finds this utterly adorable and is fighting the urge to knock on the adjoining door and fix it himself.

“Thank you so much! Promise you won’t rat me out?”

“Really, Connor, you can have the night off. I won’t tell I promise.” Oliver is smiling then.

“Thanks.”

“No problem. Have fun.”

Oliver hangs up and continues to figure out the bowtie. Connor watches the screen with a smile that almost look fond.

Michaela gives Connor an exasperated expression.

“What?” Connor asks.

“Nothing,” Michaela says then she and Asher share a look.

“What was that?” Connor asks getting slight more irritated. He’s never liked it when they act like they know something he didn’t.

“Nothing,” Asher says holding his hands up.

+

He arrives at the theatre just late enough that he can be noticed going to his seat from where Oliver and Laurel are seated. He’s wearing his best suit. It’s sleek, gray three piece that looks like it was tailor made just for him. It was.

He goes to his seat and Michaela tells him that Laurel and Oliver have totally noticed. Connor focuses on the stage and smiles a little to himself. As the musical plays on he dutifully mouths along all the lines and he even tried to be a little more emotional as he quietly sang along.

“You’re doing great.” He heard Michaela say through his earpiece.

“Is he buying it?”

“Hook, line, and sinker,” Asher says.

A sense of pride washes of Connor as it always has when he knew their plans were working as well as it was intentioned to. The familiar sense of pride is battling it out with this strange feeling of wrong-ness that he’s doing this to someone like Oliver. He wonders briefly if Oliver would fall for someone like him and not the persona he’s trying to live up. He shakes his head away from these thoughts. It’s really no use thinking about it. Who cares if Oliver is clearly falling for some made up persona and not the real him. The point is to get the job done. And at this point he’ll get the job done with a day to spare.

After the musical is done and the cast has done their bows he makes sure to leave just right before Oliver and Laurel do. It was cutting it close enough that they see him leaving but far away enough that they wouldn’t catch up with him.

He gets into the waiting cab outside the theatre.

“You did great, Connor,” Michaela says from the front seat. “We might just get through this job unscathed.”

“Or you know not more scathed than we already are,” Asher says from the driver seat. He was wearing a ridiculous old chauffeur outfit.

 “What are you wearing?” Connor asks.

“What? It’s for the character,” Asher says.

“I think he looks great,” Michaela chimes in.

Asher beams as they speed off into traffic.

Connor rolls his eyes. He looks back to the theatre to see Oliver wearing a nice suit without the bowtie. Instead he opted for a white dress shirt and over that a nice black blazer. The shirt was opened just enough to reveal a hint of chest and he’s sure it’s Laurel’s doing.

He watches Oliver’s figure grow smaller as they get farther away.

“You still know the plan?” Michaela asks breaking him away from his thoughts.

“Yeah,” Connor says getting his head back into the game. “I seduce Oliver tonight and we’re gone by morning.”

“Okay,” Michaela says.

“The plan hasn’t changed,” Connor says more to himself than to them.

“If you say so,” says Asher driving back to the hotel.

+

Connor is alone in the hotel bedroom as he watches Oliver pace around the room. He watches as Oliver takes off his jacket and run his hands through his hair.

He watches as Oliver hesitates at their adjoining door. He quickly hides his computer and waits at their door. He musses up his hair a bit and loosens his tie.

When the knocking doesn’t come he powers on and knocks himself.

The door opens to reveal Oliver’s fiancé.

“Um, hi,” Connor says.

“Hi,” the fiancé says shaking his hand. “You’re the bodyguard, Connor, right? Nice to meet you.”

“Nice to meet you too.” Connor can hear Oliver in the shower.

“Listen, I really appreciate you looking out for Oliver,” the man tells him.

“It’s my job so,” Connor starts to say but is cut off.

“Thanks again,” Oliver’s fiancé tells him and shuts the door in his face.

When the door is shut Connor groans in frustration. He decides firmly against banging his head on it repeatedly even though that’s what he wants to do and settles for resting his head on it instead. He closes his eyes and thinks of what to do next. He should have anticipated this because as with everything regarding Oliver Hampton there was always going to be surprises.

_Fuck._

**Notes for the Chapter:**

> as some of you might have noticed by now i dont know how to count so the chapter numbers keep changing. kind of want to put simon in here and cause some problems kind of want to change the guy from unknown spatula dude to simon in light of recent events? what do u guys think? 
> 
> also haven't proofread this so point out any mistakes!


	7. Day 5

**Summary for the Chapter:**

> Day Five: Wedding’s Eve

**Notes for the Chapter:**

> another update? but it's a year late. lols. but for realsies i go back to work tomorrow so im finishing up as fast as i can. also i refuse to acknowledge that i named the spatula guy jack so we refer to him over and over again as 'the fiance'

Day Five: Wedding’s Eve

Connor calls Michaela and Asher.

“What’s wrong?” Michaela asks right away when she answered the phone.

“Oliver fiancé is here,” Connor says.

“God damn it, Connor,” Michaela says.

“Hey! It’s not my fault everything isn’t going according to plan!”

“And yet somehow it feels like it is.”

“Do we have anything in the back-ups for this?” he asks a touch desperate.

Before either Asher or Michaela could answer there was a knock on his adjoining door.

“Hold on, someone’s at the door,” he says but doesn’t hang up the phone.

He opens the door to see Oliver smiling at him like he just had the best idea ever.

+

Oliver had the worst idea ever. Connor is currently driving Oliver and his fiancé to the nearest airport where the fiancé’s private jet was parked so he and his fiancé could fly to Vegas and get hitched. He tried talking Oliver out of it, but that conversation got him nothing.

“What about your wedding?” Connor remembers asking. “What about everything you’ve planned?”

“The wedding was driving me crazy! And this is just so spontaneous!” Oliver says with like a giddy smile that would have been cute if he wasn’t acting so crazy right now.

“What about Lauren? All the guests?” he tried again.

“They’ll be fine!” Oliver answered breezily. He slammed the car door as he went inside, and Connor tried very hard not to bang his head against something, again.

Connor called in Michaela and Asher as soon as he found out about Oliver’s plan and told them to do everything they can to stop Oliver from leaving.

Before he got in the car he made a quick phone call to the big guns.

Annalise picks up after four rings. “What?”

“We have a problem,” Connor was saying.

“Oh really?” she sounded far too amused for his liking.

“Yes,” Connor said through gritted teeth. Oliver was getting married he isn’t happy about that one bit. He’s losing a job after all. “I need you to stop a plane.”

“That’s a big ask,” she said simply. “And if I don’t?”

“If you don’t then Oliver gets married in Vegas and we both lose.”

“All right.”

“All right?” Connor asked. “That’s it?”

There was a click and then the line went dead.

Connor grips the steering wheel remembering the conversation with Annalise. He hopes she can pull it off but knowing her of course she can. He’s driving as slowly as he can, but Oliver and the fiancé don’t seem to notice they seem far into each other in the back of the car. That just set Connor’s teeth further on edge.

They reach the airstrip where the plan is and goddamn it the plane looks just as impressive as it did in their dossiers.

Connor tries to one final time to get across the fiancé, but he’s just kept brushing him off. Good, god he was rude. How someone as sweet and polite as Oliver be with someone as rude as that guy seems beyond Connor at this point. Sure, the guy was rich and ripped and tall but what else did he have going for him really?

He goes to Oliver who’s getting his stuff from the truck.

 “Are you sure you want to do this?” Connor asks Oliver one final time.

“For the last time, Connor, yes,” Oliver answers taking his bags from Connor. “Thanks for everything.”

Oliver gives him a firm handshake and Connor doesn’t want to let go. Oliver smiles at him one last time and he can’t think of anything that can fix this right now.

Connor watches Oliver and the fiancé get on the plane and feels helpless. He’s standing in an airstrip watching the plane take off with Oliver in it. Oliver is leaving, and he isn’t even looking back. Did he even have a chance at all in the first place?

He doesn’t know what to feel right now. He kind of wants to curl up somewhere until the weird feeling in his chest goes away. He’s contemplating calling Asher and Michaela and tell them about what happened or maybe just say it all in person when the plane turns around.

“ _Holy fuck,_ ” he says under his breath. Annalise was a miracle worker in all senses of the word.

The plane lands and out comes the fiancé and Oliver was behind him looking absolutely furious. But it’s Oliver so he looks less murder-y more _how could you_.

They get back into the car and the ride back was as tense as ever.

Oliver asks coldly to drop the fiancé off the hotel and pick up Laurel somewhere in town. The fiancé steps out and tries to say something to Oliver, but he floors it.

“So, what happened?” Connor asks genuinely concerned.

“He chickened out on me,” Oliver says. He’s watching out the window and now that he isn’t angry he just looks downright sad. Connor wants to stop the car and give him a hug. He wants a way to comfort him somehow.

“He didn’t want to get married in Vegas?” Connor can’t sound too disappointed though. Personally, he’s never thought of marriage, but he always thought getting hitched was too tacky especially, for Oliver. He deserved the best kind of wedding.

“No,” Oliver says. “He was all for it then suddenly he checked his phone and then he was all ‘we can’t do this’, ‘we need to have a proper wedding’, and ‘having a wedding in Vegas is not classy’.”

“Well, it’s not.” Connor can’t help it. He really can’t.

He’s rewarded by a very strong kick on the back of his seat.

“Shut up,” Oliver says.

“Sorry.” Connor is only slightly apologetic. He’s sorry that Oliver was so upset not so sorry Oliver was staying.

“No, you’re not.” Oliver sees right through him it seems.

“I am a little bit,” he says and sees Oliver smile a little bit in the rearview mirror.

He counts that as a win.

+

He drops Oliver and Laurel off at Oliver’s suit fitting. He lurks inside the shop for a lack of a better word. He’s behind a rack of coats watching Laurel wait for Oliver to come out from the fitting room so yeah, he’s probably lurking.

Oliver steps out of the fitting room and he looks great.

Connor can’t take his eyes away from him.

“Aww, Ollie, you look great,” Laurel says tearing up a little.

_He really does._

Oliver smiles bashfully. “Thank you.”

“Oh my god!” Laurel almost sobbed. “It might be the pregnancy, but you’re look so amazing and you’re getting married and it’s tomorrow.”

“You crying? Yes, this is definitely the pregnancy.” Oliver goes to Laurel on the couch to console her, but she bats him away.

“No, don’t,” she says sniffling. “I’m going to get snot and tears on your fancy wedding suit and then we’ll both be embarrassed.”

Oliver hugs her anyway.

“I’m so happy for you, Ollie,” she says.

“Thanks.” Oliver pulls back. “I’m so happy for you too. You and Wes and now you’re going to have a baby.”

“Yeah,” she replies almost sobs again. “I just can’t believe we get to be normal now.”

“Yeah,” Oliver says.

He’s content just watching Oliver looking wonderful in his new suit but then some consultant spooks him out of the coat rack so that moment’s over.

+

 Asher and Connor were watching Oliver, the fiancé, and the fiancé’s parents have a lovely late afternoon lunch. It looks lovely on the outside anyway he can’t really hear anything until Michaela puts the bug in on their table.

“Hey, Asher.”

“Yeah, bro?” Asher is currently acting as a bartender for today’s act. He’s doing a horrible job of bartending.

“When did you know Michaela was the one?” He feels stupid asking but the words were out of his mouth before he could filter any of it.

Asher seems surprised by the question but didn’t say anything about it.

“Well,” Asher says. “If Michaela was here she would tell you that relationships are work and it’s not just about having someone be ‘the one’ and all that crap and it’s true.”

Connor nods.

“But, Michaela isn’t here,” Asher continues. “So, I’m going to say that I knew I was in love with Michaela when she opened her opened her mouth and started telling me off.”

“So, immediately then?” Connor asks.

“Yup!” Asher smiles. “Right from the beginning.”

“That’s helpful,” Connor mutters to himself.

“Also, I have been told I would get this weird smiley face whenever I thought about her.”

“What are you talking about you have a goofy face all the time.”

“Must be because I’m thinking about her all the time.” Asher winks at him.

Connor thinks he might barf by the disgustingly sweetness of it all. Michaela saves the day by coming out of the kitchen with a tray of drinks of Oliver’s table.

“What the hell are you two talking about,” Michaela asks sharply.

“Just you, my love,” Asher says making smoochie faces.

“Well, stop it and focus,” she says sternly. “I’m going in.”

She serves Oliver’s table their drinks and plants the bug under the table slyly.

Connor moves around so he’s directly in Oliver’s line of sight. The receiver turns on and catches them in the middle of a conversation. Poor Oliver was being shredded by his future parent-in-laws. They were criticizing everything from the chairs to the menu all the way up to the flower arrangements. He tries to think up an emergency to he can get him out of there. At least his fiancé defends him a little bit but still.

Oliver meets his eyes from a brief moment and gives him a little smile. He tries not to let the fluttering in his gut get the better of him.

He doesn’t need the earpiece to hear Oliver’s future in-laws to be snide since they’re being so loud. He almost snorts too loudly when he hears them insist that Oliver and their son don’t see each other the night before the wedding.

“It’s tradition!” future mother-in-law insists. “The bride and groom mustn’t see each other the night before the wedding!”

“We’re both men,” Oliver’s fiancé says. “There is no bride.”

Connor can see that Oliver wants nothing more than the conversation to be over.

“It’s fine,” Oliver says. “We’ll sleep in separate rooms tonight.”

“Oliver,” the fiancé starts to say but then Oliver puts on a reassuring smile his way.

“What’s one night, right?” Oliver says with a shrug.

The parents seem overjoyed at least. Connor smiles to himself because that gives him the perfect opportunity for his new plan.

“What’s with that creepy smile, bro?” Asher asks.

“I don’t know what you’re talking about.”

“Sure, you don’t.”

+

Connor tails them around most of the afternoon but it’s mostly the fiancé showing his parents around the place with Oliver. Oliver charms the ever-living pants out of his future in-laws who are nice but are downright snotty and if the plan he’s been brewing is successful they won’t be Oliver’s in-laws ever.

He’s called in a couple of favors, but he knows it’ll be worth it.

He knows it’s going to work. It needs to.

+

Connor leaves Oliver as soon as he enters the hotel. He lets him stew for a little while. He also needs to make the final touches to his plan. He watches Oliver carefully on the monitor getting more and more antsy.

Asher and Michaela walk in to his room.

“It’s over,” Michaela says plopping down on the bed. “The wedding is tomorrow and it’s all over. We’re going bankrupt, we going to lose the agency, and worst of all _we’re going bankrupt._ ”

“On the bright side,” Asher says sitting beside her and rubbing her back. “Yeah, you know what I got nothing.”

“He’s on the balcony,” Connor says eyes still trained on the screen. “I’m going out there.”

“And what are you going to do?” Michaela asks.

“I have a plan.”

“Care to fill us in on that plan?” Asher inquires.

“No.” He exits the room and closes the balcony door shut louder than he intended.

“Connor?” Oliver says from the other balcony.

“Yeah?” Connor says. “I mean hey.”

“Can’t sleep?”

“No.” He looks at the view and sighs. “You?”

“I can’t either.” Oliver leans on the railing looking at the skyline.

“Excited about the wedding tomorrow?”

Oliver laughs nervously. “More like nervous.”

“Oh.”

“Terrified.”

“That’s not good.” Connor is smiling.

“Very scared,” Oliver continues laughing a little self-deprecatingly.

“You’re about to bound yourself to someone for the rest of your life,” Connor says.

“That’s comforting.” Oliver gives him a crinkly eyed smile. The light from the city glinting off his coke-bottle glasses.

“I’m just saying it’s okay to be nervous, terrified, and very scared,” Connor continues. “It’d be weird if you didn’t.”

“Maybe.”

“I have an idea.”

Oliver quirks a brow. “Oh?”

“It’s a little crazy and wild and out of the box, though. You might not go for it.”

“I need to hear all about it then.”

“Let’s go for a walk.”

“That is insane.”

“I know right.” Connor grins at him and Oliver smiles back.

“Sure, why not.” Oliver is biting his lip.

“Great,” Connor beams. “I’ll meet you downstairs.”

+

Connor gets back to the room. Michaela and Asher give him curious looks.

“What are you doing?” Asher asks.

“I’m going downstairs with Oliver and we’re going for a walk,” Connor says simply. He goes to the closet to change clothes. “Just like you heard me say on the balcony.”

“Are you sure about this?” Michaela is right behind him hands on her hips.

“Very.”

“And you don’t need us with you?”

“No.”

“No, back up?”

“Nope.”

“Not even a headset?” Asher asks.

“No headset. No anything,” he insists.

“And you’re really not going to tell us your plan?”

“I’m really not.”

Connor turns and tells them one last time. “I know what I’m doing. Just leave the rest to me.”

He’s out the door.

+

The first thing Connor and Oliver do is steal a car.

It was a nice car---vintage.

“What are we doing?”

“Going for a drive,” Connor says with a smile.

“What happened to taking a walk?” Oliver asks but gets in the passenger seat anyway.

“It’s more fun taking a walk in a car don’t you think?”

Oliver laughs and agrees. “Definitely.”

They speed off into traffic leaving everything behind them.

“Where are we going?” Oliver asks sometime later.

“It’s a surprise,” he answers.

Oliver seems satisfied with the answer though.

They arrive in a back alley somewhere and he parks the car there.

“What are we doing?” Oliver gets out of the car and eyes the alley wall.

“We’re going to jump the fence,” Connor answers simply. He adores the look of confusion on Oliver’s face.

“That fence?” Oliver points at the fence. “We’re going to jump that fence right there?”

“Yup.”

Oliver looks at Connor like he’s just now having second thoughts about this then he shrugs and says, “After you.”

“You don’t think I can scale a fence, can you?”

“I really don’t think you can.”

Oliver makes a gesture for him to move on. Connor maybe puffs up his chest a bit and goes to scale the fence. Halfway through he struggles a little bit.

“You doing okay over there?”

“Perfect!” he calls down. “You enjoying the view from down there?”

“Could be better.”

Connor sputters a bit and then finally falls over to the other side of the fence.

“You okay?”

“I’m fine! Just get up here!”

Oliver goes over the fence without any incident which is, frankly, unfair. He’s adorably cute and incredibly fit. It’s unfair.

Connor leads Oliver forward until they reach a locked gate Connor opens effortlessly.

“We stole a car and now we’re breaking and entering,” Oliver says.

“Stealing would mean we won’t return it later. We’re borrowing the car. But yes, we are breaking into here.”

“What is here exactly?” Oliver steps in following Connor inside.

“You’ll see.” Connor puts a hand on the small of Oliver back.

Connor leads him over to a corridor where the tunnel aquarium is. He asked the nightguard to keep it open for them and have a little bit of romantic lighting.

“Should I keep my eyes closed for this or something,” Oliver asks quietly.

“Good idea,” Connor says almost whispering in Oliver’s ear.

Oliver tries to repress a shiver.

Once they were under the aquarium tunnel he tells Oliver to open his eyes.

A small gasp comes from Oliver and his face breaks into a small. Connor doesn’t take his eyes away. Oliver looks around the swimming fishes moving all around.

“Oh wow,” Oliver whispers.

“Yeah,” Connor agrees still looking at Oliver. “Wow.”

“This is.” Oliver looks back at him smiling so bright it actually lights up the room. “Amazing.”

“I knew you’d like it.”

“How’d you get in this place?”

“I know a guy,” Connor answers with a shrug acting nonchalant.

“You bribed the nightguard.”

“I did bribe the nightguard. Yes.”

“So, we really didn’t have to park in the alley and jump the fence, did we?”

“No, but it’s more fun that way isn’t?” Connor grinned at Oliver.

“Definitely.”

“Is that a stingray?” Oliver points at the sea creatures swimming above them. 

“Yes, it is.”

“It looks so strange.”

“That’s how they’re supposed to look.”

“Poor guy.”

“No, it’s doing fine. I mean look it’s the star of the show.”

“I guess, you’re right.”

It really is something that Connor has found the one person on the planet that would feel bad for funny looking sea creatures. Connor is distracted looking at Oliver when the nightguard that was definitely not the guy he bribed.

“Hey! No one is supposed to be here!” the guy yelled.

“Oh shit,” Oliver says.

“Let’s go!” Connor tugs Oliver arm and they run away back to the alley, over the fence, and in the car.

They speed off back into traffic to the city.

“You hungry?” Connor asks.

“I could eat,” Oliver shrugs.

+

Connor drives them to a little restaurant. It’s the kind of restaurant known only by word of mouth and it was as homey as it gets. He’s already called the owner beforehand and told him to keep the place open for him.

They arrive at the small Italian place and it looked as quaint as he remembered. There were small fairy lights surrounding the outside.

“Looks closed,” Oliver says.

“It’ll be open for me,” Connor assures. “Don’t worry.”

“I have a feeling you planned this beforehand.” Oliver eyes him suspiciously but still has that smile so it’s probably in jest.

“I live to anticipate your every need,” Connor says with a flick of his wrist.

Oliver laughs, and something breaks open in Connor’s chest. He’s going to make most of tonight. Whatever it takes he’s going to make Oliver remember this night forever. He has to.

Before he can knock on the door. His restaurant owner friend opens the door and ushers them in.

“Don’t take anything and lock the door when you leave,” she tells him. She smiles at Oliver who gives a small shy wave. “Don’t burn the place down.”

“I won’t,” Connor promises.

“Good luck,” she tells him before leaving them in the restaurant alone.

Oliver watches her go and turns to him.

“So, we’re alone in an Italian restaurant.”

“Yes.”

“What’s next?”

“Isn’t it obvious, Ollie?” The nickname just slips out, but it feels right, and it makes Oliver blush which is a plus. “We’re going to make pizza.”

+

They’re wearing aprons and there’s flour everywhere and Oliver is giggling like a school kid.

“Is there something on my face?” Connor asks trying to look stern.

“No,” Oliver chortles. “Not on your face. Your hair, your clothes, your everywhere else though…”

“Really?” he takes a pinch of flour and throws some in Oliver’s general direction.

“Hey!”

“You have a little something on your face.”

“You would know.”

Connor smirks at Oliver and then throws more flour in his face only for Oliver to retaliate with some grated cheese.

“Okay, now you’ve started a war!”

Connor grabs the ladle for the tomato sauce and wields it like a sword splattering both of them liberally with tomato sauce.

Oliver grabs the sack of flour and throws more at Connor’s face.

They continue wasting food for a couple of more minutes before they just dissolve into laughter.

“Now, I really am hungry.” Oliver takes off his glasses and tries to wipe some gunk off the lens.

“Here let me.” Connor takes the glasses from Oliver’s and wipes it down with a paper towel. He puts it back on again for him. Oliver is looking at him and chuckles.

“What?”

“This isn’t the first time you’ve done this you know.”

“What touch your glasses?”

“Yeah,” Oliver says. “Do you have a thing for glasses or something?”

“Maybe,” Connor hums. “Or maybe I wanted an excuse to touch your face.”

“Ah.” Oliver cheeks blush and he looks away. “Come let’s make some pizza. I’m starving.”

“Right. On it.” Connor gets the dough and he starts putting sauce on them.

He started putting cheese and pepperoni on his while Oliver started putting ham and pineapple on his.

“What the hell are you doing?” Connor asks appalled.

“Topping my pizza?”

“No, you’re ruining it.”

“That’s an overreaction.”

“It’s really not. What the hell.”

“It’s pineapple and it’s good.”

“And it’s staying the hell away from mine.”

“Pineapple on pizza is good and you cannot take that from me!”

“No one is trying to take that away from you.” Connor assures with a snort. “You can have that all to yourself.”

Oliver looks at him determined. “You’re going to have a slice of this pizza when it’s done.”

“I am not!”

“Oh yes,” Oliver says resolutely. “And you’re going to like it and you’re going to be amazed.”

“No way.” Connor is shaking his head vigorously which makes Oliver laugh.

“Yes way! You’ll see!” Oliver says enthusiastically and puts both of the pizza trays in the oven.

+

Connor and Oliver sit on the counter watching the oven bake their pizza sipping soda in wine glasses because his friend locked the liquor cabinet tight. Smart move. They’re sitting close enough that their thighs are pressed up next to each other.

Connor fills Oliver’s glass with the last of the first bottle of soda and says, “Married within the year.”

“Hm?”

“Last drop means you’ll get married within the year,” he explains.

“I’m pretty sure that’s for wine,” Oliver says. “Also, the wedding is tomorrow so wish me something else.”

Connor raises his glass. “Two a beautiful love story, then.”

Oliver looks at his raised glass and then at Connor. “To an interesting love story.” Then clinks their glasses together.

“Cheers,” Connor murmurs.

“Cheers,” Oliver says back.

The oven dings.

+

The pizza is piping hot and really good.

“C’mon just eat it.” Oliver is holding his pizza slice to his face.

“Stop it,” Connor reprimands without any real bite since he’s smiling like a fool.

“You promised. Just one slice. One slice and then you can curse it forever and ever.”

“Fine. Fine. I give. I give.” Connor opens his mouth and Oliver practically shoves the slice in his mouth.

Connor chews dramatically giving little nods here and there. Oliver is watching him with rapt attention.

He finishes his gigantic bite and looks at Oliver.

“Well?” Oliver needles.

“It’s not that bad,” Connor lies.

Oliver smiles at him big and toothy. “You hate it.”

“So much.”

“I tried.”

“You gave a valiant effort.”

They continue to eat and chat for a little while more. He lets his touches linger. He sits too close. He looks all he can. He tries to memorize the way Oliver smiles and the sound of his laugh. He tries to etch it forever in his brain. He never wants to forget the way Oliver looks in this dimly lit restaurant eating pineapple pizza laughing at his dumb joke. He doesn’t want to forget anything from this night or any time he’s spent with Oliver. He hopes after all this he leaves Oliver with good memories. He wishes more than once that this night never ends.

“Have you ever been in love?” Oliver suddenly asks.

“I thought I was before,” Connor answers. He wouldn’t normally answer questions like this, but he can’t lie to him now. Not after everything he’s built up has been a lie.

“What happened?”

“There was this guy in boarding school and I guess he could count as my first love. I was crazy about him and I thought he was crazy about me too. We went out and we were for all intents and purposes together.”

“But?”

“But then you know things fell apart when after summer vacation when he suddenly announced he had a girlfriend.”

“Wow.”

“Yeah. It hurt so bad. I thought he just played me and strung me along. I never talked to him again and avoided him for the rest of the school year. So, after that I swore off anything resembling to feelings.”

“How’d that work out for you?”

“Pretty well but then things happened.” Connor looked directly at Oliver then. “Then I met someone, and I realized that I probably wasn’t in love before.”

“What happened next?”

“I don’t know yet.”

Oliver’s phone rings shrilly defusing the tension in the moment. Connor sees it’s the fiancé calling and let’s Oliver step away. He moves to the jukebox and looks for a song while listening in to Oliver’s half of the conversation.

“Hello? Oh yeah… No, I’m just with Laurel… She insisted we go out one final night… Go back to sleep you shouldn’t even be in my room anyway… Yeah, I’ll be back don’t worry… Okay, bye.”

“The ball and chain calling?” Connor tries to joke lamely.

“Yeah.” Oliver turns off his phone. 

“So, you wanna dance?” Connor holds out his hand.

Oliver takes it with no hesitation.

He swings them around and twirls Oliver around.

“That was fun,” Oliver says as they sway to the music slowly.

Oliver then spins him around and dips him.

“You can dance,” Connor exclaims breathless.

Oliver rights them gives him another twirl.

Connor holds him closer.

“Yes, I can. Now, so can you.”

Connor wraps his arm firmly around Oliver’s waist and the other holding Oliver head close. He hides his face in the crook of Oliver’s neck and they just swayed to the music. The world around them slowed down and it felt like it can go on for eternity. Connor closes his eyes and let’s himself get lost in the moment. If this was all Connor was going to get then he was going to get whatever he could.

+

They’re driving back to the hotel with Oliver at the wheel with the top down.

“I think it’s going to rain.” Connor squints up at the sky.

“It probably is,” Oliver agrees. He presses a button so the top goes up before they get drenched.

Oliver parks their stolen car right in front of the hotel but no valet or concierge comes up to them. There was only one car on the pick up strip.

“What?” Connor notices Oliver looking at him.

“Nothing. It’s just your face,” Oliver explains.

“Do I have a weird smiley face going on?”

“A little bit. Yeah.”

“It happens.”

“Thank you by the way,” Oliver says. “For tonight. For everything. I can’t imagine a better night. I know it’s weird that I barely know you, but I feel great when I’m with you.”

“I just told you one of the most poignant points in my life,” Connor says. “You have been a closed book.”

“That’s fair,” Oliver says then looks out the window. He takes off his glasses and rubs his eyes.

Connor takes the time to take in the details of Oliver’s face.

“There was one year in my life that I went missing,” Oliver says. “Like my family couldn’t find me and fell off the face of the planet missing. That was the year I met Laurel. We were both in this like gang together.”

“A gang?”

“Yeah. We were doing some really illegal things. Like hacking into banks and the government. We were like these hacktivists.  We’d go online and blackmail these execs to do the right thing. I was having the time of my life. Everything was so exciting and everyday was an adventure.”

“What happened?”

“I hacked into my parents’ bank account once and found out somethings that I didn’t know about my family. Then my step-mother found out about it and threatened to call the feds on us or worse so, we disbanded, and I was forced to go home.”

It made sense now to Connor as to why Bonnie Winterbottom didn’t want this wedding to happen. If Oliver spilled the beans to his high-profile fiancé then they’d all go down probably in flames. But here’s the thing she doesn’t know about Oliver. He would never do that. He wouldn’t even think of doing it. The one time in his life that he let loose and did something bad and it was for a good cause.

“Ollie.” Connor didn’t know what else to say.

“Didn’t expect that did you?” Oliver asks giving a humorless laugh.

“No.” Connor smiles. “You’re just full of surprises. I never know what to expect from you.”

“I have to keep you on your toes,” Oliver teases.

“You have been since day one,” Connor retorts. “I feel great with you too. Tonight’s been perfect.”

They stay like that for a little while looking at each other the rain pouring down around them.

+

Annalise Keating and Bonnie Winterbottom watch from a parked car as Oliver and Connor get out of their car and to the hotel.

“I told you he’s a pro,” Annalise tells Bonnie.

“Let’s just hope he can bring it home,” Bonnie says as they watch on.

+

Connor and Oliver reach the hotel doors when Oliver stops and tugs Connors hand. Connor turns and face Oliver. They’re so close.

Connor reaches up and pulls Oliver closer. He tilts his head up to kiss but before their lips get a chance to meet he rest his head against Oliver’s and sighs.

Oliver pulls away and looks at him. A little confused and a little hurt and it’s makes Connor feel like shit.

“Thank you,” Oliver says and walks away.

Connor watches him enter the hotel wishing he’d look back.

+

“What the hell was that?” Bonnie asks outraged.

“He’s an idiot,” Annalise says simply.

+

Oliver finds him by the pool and sits next to him dipping his toes in the water.

“You should be getting ready,” Connor says. He doesn’t know what he’s saying really. All he feels now is just hollow.

“I don’t want to go through with it,” Oliver says and Connor’s heart leaps. “I want to cancel the wedding.”

There’s silence. Connor doesn’t say anything. He doesn’t know if he can.

“Did you hear me?”

“Yes.”

“Well?”

“I think you should get married,” Connor says through gritted teeth. This feels like pulling teeth but he’s doing it for Oliver’s own good. He deserves the perfect life with the perfect guy and the perfect everything and his stupid private jet. “I think you should live the life you’ve set out for yourself.”

“Connor.”

“No, listen,” Connor bulls ahead throwing his heart into the fray. “About last night. It was great, but that’s all it is. One night. Just go through with your wedding and be married and happy and go on with your life.”

He can feel Oliver looking at him but doesn’t say anything.

“Okay.” Oliver stands up and leaves.

Connor stays there for a while. Alone.

**Notes for the Chapter:**

> one more chapter guys! then this 2 year fic is finally over! it will finally end and you'll all be free!


	8. Day -1

**Summary for the Chapter:**

> Day -1: The Wedding Day

**Notes for the Chapter:**

> it's here! the final chapter! after two years! lower ur expectations

Day -1: Wedding Day.

Connor is in his room when Annalise calls. He’s sort of expecting that she would call sooner or later. He would have preferred it to be never but as it’s drastically clear as the past few hours have made it, he doesn’t always get the things he wants. No matter how much he wants it.

“Your mission is over Mr. Walsh,” Annalise says cutting straight to the point.

“I know,” Connor says as detached as he could. He knows it abundantly well.

“You’ll get your money,” she assures coolly mistaking his tone for something else entirely.

“I don’t care.” He hangs up. He really doesn’t. He feels a little sick and a whole lot of numb.

The job was over and he’ll never see Oliver again. He almost regrets giving Oliver his real name because now when he thinks about the man who gave him the perfect night and then left him anyway he’ll think of Connor. He’ll think all about Connor. He guesses that was just as well since, really, isn’t this supposed to be a game to him in the first place? He didn’t expect to get attached. To catch feelings. To fall in love.

He’s thinking about whether he should just tell Michaela and Asher about what happened last night or just take it to his grave. Keep the memory of his perfect night with Oliver to himself. Keep it close to his heart and never let it go.

As he was face down on his bed contemplating about what he should do next Michaela and Asher barge into his room and sat down on either side of him.

“What happened, bro-bro?” Asher asks gently.

Connor wants to hate Asher for coddling him at a time like this but he really doesn’t have it in him. He feels so tired.

“I told him to get married,” Connor says.

“Why would you do that?” Michaela asks like it’s the stupidest thing he’s ever done. It probably was but it is also the most selfless thing he’s ever done so there’s that. What catches his attention is that her tone is much kinder than what Connor expects. It makes his heart twinge.

Is it that obvious that he’s been all wrung out? If Michaela is being nice to him then he obviously looks as horrible as he feels. He wants to burrow further into the sheets and disappear.

“It’s the right thing to do,” he says simply. It is. It’s the right thing to do and it’s the hardest thing he’s ever done.

“We should be proud. We’re letting Oliver marry the perfect man. We did the right thing,” he insists. He needs to say this over and over again. He needs to make himself believe that it is the right thing to do. He needs to forget the way Oliver looked at him before he left and the things he said. Oliver didn’t know what he was doing but Connor did. So, Connor needs to be the one to do the right thing.

“When have we ever been a stickler for doing the right thing?” Michaela says.

“Since now,” he replies. “Since Oliver Hampton.”

+

Connor is quiet the whole time while they pack their surveillance stuff and dossiers. He avoids lingering on the pictures of Oliver they’ve captured before this job and just stuffs them into his duffel. He ignores the looks Asher and Michaela are exchanging when they think he’s not looking. They should be happy. They didn’t accomplish the mission but they’re still getting paid. It can pay for all their debts and then some. They’ll finally be free them from this stupid line of work. The money is enough to leave this all behind because after that’s happened does he really want to keep doing this? People can get out of their own stupid relationships without his help.

“You ever going to tell us what happened last night?” Michaela asks.

“It doesn’t matter,” he says dismissively. He wants this day to be over and done with. In a few hours Oliver is going to be officially married to the perfect guy and he’ll be back to his old life.

“Are you sure about that?” Asher says.

He lets out a deep sigh. He doesn’t want to deal with this right now. Or ever. He isn’t good with dealing with things like this. Years of avoiding it has made him uncapable of handling this in any other than trying to forget it.

He doesn’t want to forget it though. He wants to remember everything about this. The good parts and the bad. What gets him the most is that he and Oliver weren’t anything other than a possibility. He doesn’t know how to get over something that is just what could have been and now will never be.

Connor doesn’t answer. Instead he says, “I’ll wait for you downstairs.” He just zips up his bags and leaves.

+

“Do you agree with Connor?” Asher says to Michaela after Connor leaves the room. “Do you think he did the right thing?”

“No.” Michaela shakes her head. “I really don’t think so.”

“I totally agree.” Asher smiles. “So, what are we going to do about it?”

“Nothing we can do now.”

“Oh, c’mon you don’t believe that. There’s always something. You’re Michaela Pratt genius problem solver extraordinaire! There has to be something!”

“If Connor doesn’t want to do anything then we should respect his wishes.”

Asher gives her an affronted expression and she smirks. He beams at her when she sees it.

“I have a plan,” Michaela says.

“I love it already,” Asher beams.

+

Connor steps out of the elevator and into the lobby just in time to get a glimpse of Oliver leaving the hotel and getting into his car. Oliver is wearing the same white suit he saw during the fitting. He still looks as amazing as he did that day. Maybe now even more so. He’s always had a thing for things he can’t have. This time it’s a lot worse since he could have had it but he turned it away.

He’s got half a mind to run over there and---- Do what exactly? What would he do? Would anything be enough? He chose to let go. He’s got to live with that.

The elevator dings and Michaela and Asher step out.

“Are you ready to go?” Michaela looks at him with an arched eyebrow.

His stomach twists but nods. “Let’s get out of here.” And never look back, he doesn’t say.

+

Connor and Michaela wait for Asher to get the car outside the hotel. Michaela is quiet the whole time which is unlike her but Connor can’t think too much about it. Maybe she’s glad the job is over but doesn’t want to rub it in. As for him he’s anxious to get on the plane and go back the life he’s known.

“Did Annalise say anything else to you?” she says breaking the silence. “About the wedding and Oliver?”

“I don’t know I hung up before she could.”

“You hung up on Annalise?” Michaela’s eyes widen in shock. Rule number one is that you never hang up on Annalise unless you want a death wish. In his defense he didn’t want to hear whatever she wanted to say. Whether it was words of comfort or just good old-fashioned pity. Knowing Annalise, it was probably a mix of both but with a heavy ladling of the latter.

“What else is there for her to say?” Connor is so very tired of this.  “She told me we were still getting paid and that’s what matters right?”

Michaela sighs clearly exasperated. “If you say so.”

+

Connor sits at the back of the car. Michaela is up in front and Asher is driving. They were a little too early for their flight but it’s just as well. He watches the city pass by. He tries to regain his composure. He tries to build back up the walls Oliver unwittingly knocked over in their too short time together. He’s much too lost in his own thoughts to notice where that they are going the wrong way for the airport.

“Asher, this isn’t the way to the airport,” Connor says. Where the hell were they going?

“Oh, isn’t it?” Asher asks innocently still not changing directions.

“Where are we going?” he demands. He looks around at the road again and it strikes him as familiar.

“Haven’t you figured it out yet?” Michaela says impatient. “We’re getting you to Oliver’s wedding.”

+

Oliver is sitting in a car with his father. The car ride was relatively silent the moment they got in.

“Are you sure about this?” Oliver’s father asks. He already knew the answer but it never hurts to be crystal clear.

“Of course,” Oliver says. “It’s the surest I have ever been in my life.”

Oliver looks ahead. He believes that whatever happens next is for the best. He knows it with all his heart.

+

“What?!” Connor shouts. “Asher stop the car! God damn it, Asher! STOP THE FUCKING CAR!”

He lunges forward for the steering wheel, but Michaela bats him away and pushes him back down. She stares him down and glares right back.

“Connor! Stop! Do you want us to crash and die?!” Michaela shrieks. “What the hell is wrong with you?!”

“What’s wrong with _me_?!” Connor shouts back. “What the hell is wrong with the two of you?! We are not going to that wedding! Turn this fucking car around!”

“Calm down, man!” Asher says. He keeps driving like Connor is not freaking out.

His heart is racing. His throat feels like it’s closing in. His chest is tightening. He feels dizzy all of a sudden. He thinks he might be having a panic attack. He takes in a shallow breath. He is most definitely having a panic attack.

“Don’t tell me to calm down!” He breathes hard. “God damn it just leave this alone! I’ve had enough of this! Turn this fucking car around and get on our flight and just leave! The job is over! It’s done! There’s nothing we can do about it!”

“There’s always something we can do!” Michaela says.

He tries to grab the steering wheel again only for Asher to swerve the car violently off the road effectively throwing him out of balance and right to the back of the front seats. He hit them with a loud thump.

“Ow,” Connor says at the floor of the car. “What the hell was that?”

“What are you doing, Connor?” Asher asks and he sounds a little mad.

If anyone should be mad it should be Connor. He’s the one being manipulated into doing something, he doesn’t know what.

 “What do you mean? We finished the job. We’re doing what we’ve always done after a job. We’re finally going to go back home to our own lives.” He gets up off the car floor and sits down warily.

“You mean _your_ little life? With your random hook-ups and your what was it, your ‘I don’t do feelings’, ‘I don’t do boyfriends’ bullshit? Your short-term love stories?” Michael says furiously. “Do you really want to go back to that?”

He hangs his head. He closes his eyes and buries his face in his hands. Michaela sighs heavily and sits back down hard. Her reading him out like this really took it out of her.

“Well, Connor?” Asher asks expectantly.

He groans into his hands. “I don’t know.”

“What do you mean you don’t know?”

“I mean.” He sighs. Why was everything so messed up. “I don’t know.”

“It’s a shame you know,” Michaela says looking out the window. “The one time you find someone you really like and you just…” she trails off.

“Yeah,” Connor says. “But he’s---”

“He’s what?” Michaela goes on. “He’s too good for you? He’s too nice? He’s a much better person than you? You don’t deserve him? Which is it?”

“All of it.” Connor drops his head on the headrest his eyes closed. He can’t handle the twisted feeling in his chest. “Just. All of it.”

The car is silent for a few moments before Asher decides to break it.

“How was last night?” Asher asks quietly. “You don’t have to tell us what happened. Just, you know, how was it?”

“It wasn’t real,” he tries to say firmly but it comes out as sad even to his own ears.

“Wasn’t it?”

“Of course, it wasn’t. I was playing a part! None of it was real!”

“And if it is?” Asher challenges.

“What do you mean?” Connor doesn’t understand what Asher was getting at.

“Connor,” Asher says patiently. “Look, man. I get that you’ve never dealt with feeling your entire life but just admit to yourself that this is real and do something about it!”

Connor doesn’t say anything. He lets what Asher said sink in. Asher is right no matter how much even thinking that makes him want to cringe. Asher is right. He needs to face his feelings.

He takes a deep breath and in the silence of the car, with the noise of the busy cars passing them by, he finally hears the sound of his heart breaking.

He lets himself feel it and it much worse than he remembers from last time. The difference now was that he doesn’t regret anything. If he’s asked to do it over again knowing that he’s just going to end up with his heart in pieces all by his own doing he’d still do it. He’d do it with no moment’s hesitation. If a broken heart is the price he pays to be with Oliver Hampton even just for five short days then he’d give that and then some.

He’s always been so careful about his heart. Now, he feels like he’s up in the air. He laughs a little. He’s abundantly aware now why it’s called falling.

“It doesn’t matter anyway,” Michaela says casually like Connor isn’t having an emotional breakthrough in the backseat. “You’re just going run away from this like you always do. Right?”

“Well, Connor?” Asher asks. “Is she right?”

Is she right? He knows he runs away from things like this. He’s always done and he thought he’d always do that. But things have changed. He’s changed. He knows what he’s going to do.

“Let’s go,” Connor says.

“What are we doing?”

“We’re crashing Oliver’s wedding,” he states firmly with renewed conviction.

+

Asher is driving through the highway in a speed that is very much illegal. The wedding will start any minute they need to get there before the couple say their ‘I do’s’. He’s flooring it as hard as he can but the car can only do so much.

Connor’s heart is racing but this time it’s not from the crushing despair of losing something he had no right to have in the first place. This time because he’s finally ready to fight for something. Just as he had this fantastic surge of determination when the car suddenly slows down and the traffic around them stills.

“No, no, why are we slowing down?!” Connor yells as their car pulls to a stop.

“I don’t know,” Asher says looking at the road in confusion. “I think there’s a pile-up or something. Either way traffic isn’t moving.”

Before Asher can finish that sentence, Connor is already half-way out of the car.

“I’m going to get there myself,” Connor says. He slams the door shut and looks at Asher and Michaela.

Michaela rolls down her window and says, “Good luck, Connor.”

“Thank you.” He smiles. “For everything.”

“You’re welcome,” Michaela says.

Asher gives him two thumbs up and a goofy smile.

“Well, what are you waiting for?!” Michaela asks. “Run!”

“Right!”

Connor looks at the road ahead. A road that will lead him to something that will probably change his life forever and takes off.

He runs at full speed with no hesitations.

He can do this.

+

Asher and Michaela watch as Connor run up the hill to crash Oliver’s wedding. When Connor’s figure disappeared from their line of sight the traffic began moving again. Much quicker than expected.

“So, apparently there isn’t a pile up,” Asher says as he puts the car in gear. “He probably shouldn’t have gotten out of the car.”

“That’s fine,” Michaela replies. “He deserves to sweat a little.”

Asher holds out his hand and Michaela takes it with a smile. They drive on take the long way around.

+

Connor Walsh is smart, clever, and extremely pretty. He is also arrogant, distant, and can’t handle his own emotions very well. He is a professional couple breaker and today his heart got broken.

But he’s trying to fix that.

Connor is running as fast as his legs can possibly take him. He silently thanks the stars for the past few days because his running has drastically improved. He thinks of Oliver and runs faster. He appreciates the feel of the wind on his face. It helps him clear his mind.

He running to Oliver. He’s running to that wedding and he’s going to spill his guts. He’s going to tell Oliver how he truly feels. He’s going to tell him everything. He’s been thinking about what Oliver deserves all this time and now it’s clear. He deserves the truth. He’s going to tell him the truth about all of this. All the lies he’s spun. All the schemes he’s put up. Everything single thing.

He’s going to give them a fighting chance. Even if Oliver turns him down once he said everything that needs to be said, especially then, it will be okay. He can’t know what Oliver really wants but at least now he’s giving him a choice.

It’s okay if Oliver doesn’t choose him.

It really is.

At the end of the day if Oliver is happy then Connor can learn to live with whatever happens next. But now that he knows he’s falling he hopes Oliver catches him.

+

Connor arrives at the wedding venue at the edge of the cliff panting and exhausted. He rests his hands on his knees and takes a moment to catch his breath.

He takes deep breathes to calm his nerves. His palms are sweating but that’s okay because the rest of him is already sweaty. He takes note of the important things he wants to say. He breathes in deep, lets it go, and stands up straight.

The venue is empty. The chairs are set up but the place was half decorated. He thinks for a second that the wedding is over and he missed his chance. He pushes that fear way down and looks for any clues as to what the hell is happening.

He walks down the aisle slowly mystified. He walks further sees someone alone in the gazebo and stops when he realizes who it was.

“Oliver,” Connor calls.

Oliver turns around and looks genuinely happy to see him. “Connor.”

“Hi,” he says dumbly. Everything that he planned to say suddenly went out the window.

“Hey.” Oliver smiles.

“Is the, uh.” He swallows unsurely. “What happened?”

“I cancelled the wedding,” Oliver says simply.

Connor is tempted to jump for joy, maybe sing, when he hears Oliver say it. He doesn’t want to get ahead of himself.

“I told you not to.” Connor steps closer hesitantly.

“I’m bad at listening to you.” This time it’s Oliver who steps closer. “I thought I made that clear the second day we met.”

“You did,” he says with a laugh. “My calves still feel it.”

Connor takes the time to look at Oliver in his fancy suit but without his glasses. Was Oliver waiting for him in the gazebo? His heart flutters with the thought.

“Were you waiting for me?”

“A little bit yeah.” Oliver looks away shyly.

Connor beams. Then he steels himself for what he came here to do. “I have to tell you something.”

“Connor---”

“No, please hear me out. I really need to tell you this and if you don’t let me say it now I’m probably never going to find the courage to say it again so can you please?”

Oliver bites his lip. “Connor, if you---”

“Please?” he practically begs.

He wonders what he must look like. Sweating, tired, and really sleep deprived only recently coming to terms with the fact that he has feelings.

“Okay.” Oliver nods. “Go ahead.”

“Thank you---”

“But after I get to tell you something,” Oliver says.

Connor can’t believe it but he smiles. “Whatever you want.”

“Say what you want to say.”

Connor takes a deep breath. “I’m not really a bodyguard. But I really was hired by Bonnie but not for the reason you might think.  I was hired to break you and your fiancé up by making you fall in love with me instead. I usually don’t break up couples that I think are doing well and you two were doing pretty well but I’m broke and me and my team, I have a team by the way, really needed this job so we took it.

We devised scheme after scheme and made up lie after lie. We tailor made each one in the hopes I can seduce you faster.”

“Connor, I---,” Oliver starts to say but he keeps going.

“Ollie, please let me finish.” Connor continues, “You remember that time you got robbed and I saved the day? Yeah that was us. That time with your room and the repair man was also not real. The time we went for a jog and the thing at the bridge also lies.”

“You don’t have to---” Oliver says again.

“No, I do have to. Oliver, please just listen.” Connor keeps going and says, “When I saw you at first, I thought it’d be an easy job but then I actually got to know you. You’re unpredictable and you surprise me at every turn and good god I have never actually met someone who is as genuine and as nice as you are. I didn’t realize _I_ was the one falling in love. By the way, Ollie, if it still wasn’t clear I’m in love with you.

That night we had together. That was real. All of it. I do hate pineapple on pizza. I did get my heartbroken and closed off for a while. I’m really bad at relationships but if you can just give us a chance.” He swallows. “I know I’m probably not good enough for you and you are by far too good for me but I will do everything I can to make you happy. From bribing the wrong nightguard to let us in the aquarium to anything you can think of. If you let me.”

Connor is met with nothing but silence and he feels his chest tightening again.

“That is,” Connor says. “If you aren’t furious with me right now. I would understand if you are. And if you never want to see me again.”

“I’m not mad at you,” Oliver says taking a step closer to him. “I don’t think I could ever be mad at you that I never want to see you again.”

“Even after now that you know everything?” Connor feels hope blooming in his chest. Oliver isn’t cursing his name and telling him off. He was even smiling a little bit when Connor was spilling his guts.

He lets a hopeful smile slip and Oliver returns it tentatively. At each and every turn of their journey together Oliver always surprises him, but Connor never expects what Oliver says next.

“I know, Connor,” Oliver says. “I’ve known the whole time.”

“What?” Connor should have seen something like this coming. He can’t believe that even after all this Oliver can still surprise him. “What do you mean you’ve known the whole time?”

Oliver looks away hand coming up to rub the back of his neck.

“Remember when I said I was a hacktivist?” Oliver asks nervously. “You know and the fact that I like hacking into things?”

“Yes?” Connor didn’t intend it to sound more like a question but it does anyway. He knows where this is going now but he wants to hear about it anyway.

“That day when I ran away from you,” Oliver says. “I used that time to research you and try to know everything about you I could find. I’ve some pretty interesting things.”

Connor’s mind quickly flashed to some questionable dating sites he’s joined in the past and was quick to defend himself. “Don’t believe everything you read online, Ollie. I’m a changed man.”

That makes Oliver smile which leads Connor to believe he knows exactly what he’s pertaining to.

“I found out you weren’t a real bodyguard and that you’re apparently a professional couples breaker. I also know you’ve been working for Annalise and Bonnie. And that you’re on the verge of bankruptcy.” Oliver reaches up to his face only for him to remember that he’s not wearing his glasses.

Connor finds his nervous tick adorable still. Love is making him such a sap.

“So, you knew everything? This whole time?” Connor asks. He is a little bit amazed by the turn of events.

“I didn’t know _everything_. Just that you weren’t what you said you were,” Oliver clarifies. “Some parts. At times when--- the way you looked at me sometimes. I don’t know. I was never sure. Then that night happened and I just let it all go. I just let myself feel the things I did for you.”

Connor can’t believe this is happening. He wonders if he actually just passed out from exhaustion and this is a dream. If this is a dream he doesn’t want to be woken up.

“I wasn’t sure if everything up until then was just still a game to you or a means to get the job done,” Oliver continues spurred on by Connor’s silence. “But I was falling for it, for you, anyway. And I didn’t know if any of it was real until you told me to get married.”

Connor looks at him. Just really looks. He tries to decide what he should feel right now. He was lying this whole time but this whole time Oliver was just playing along instead of being played. It makes him feel better somehow. Like all this time he thought he was alone in this when he was never alone.

“Are you mad?” Oliver hedges uncertainly. Connor is sure that if Oliver had his gasses he’d be worrying over it now. “I understand if you’re mad and that you never want to see me again.”

Connor chuckles at that. “Now, you’re just using my lines back at me.” He’s smiling at Oliver, now. He didn’t think he could fall even more in love than he was minutes ago. He’s always happy to be proven wrong by one Olive Hampton.

“You’re laughing at me,” Oliver accuses with a pout. “I didn’t laugh at you when you were spilling _your_ feelings.”

Connor’s cheeks hurt from smiling so hard. He crosses the distance between them because he suddenly can’t take being so far from Oliver anymore. Oliver meets him halfway much to his joy. Once Oliver was within grabbing reach he wraps his arms around his waist and burrows his face into the crook of Oliver’s neck. Oliver just holds him close.

If this is what it feels like to be loved back then he knows now for sure why people fight for something like this so hard.

“I was wondering if you were going to show,” Oliver whispers into his hair. “Also, you’re really sweaty.”

“I’m sorry,” Connor mumbles into Oliver’s neck. He feels Oliver shiver and he stops himself from getting things off track and kiss a trail on it. “I ran all the way here.”

Oliver pulls back which Connor did not like it at all but let it happen. “You ran all the way here?”

“I don’t mind running,” he says. “As long as it gets me to you.”

Oliver smiles at him adoringly and the butterflies his been ignoring these past few days swarm.

“Were you waiting for me, here weren’t you?”

“Yes.”

“Why?”

“I hoped you’d come crashing into the wedding. You do have flare for the dramatics I’ve noticed.”

“Yes, well, while we’re being honest I got goaded into crashing the wedding,” he confessed.

“Thank god for meddling friends, I suppose.” Oliver says and it makes Connor giddy.

“If I didn’t try to stop the wedding what would you have done?” he asks suddenly.

“I’d have found you.” Oliver says with certainty. “And if you didn’t get bullied into crashing the wedding what would you have done?”

“I’d have lived my life in misery,” he says gravely.

Oliver snorts then that turns into a laugh.

“That’s the worst thing I’ve ever heard come out of your mouth.” Oliver is shaking with laughter now. “Please, tell me that’s scripted.”

“Nope.” Connor grins. “All me.”

He inches his head closer and leans up, finally, into a kiss.

He’s read plenty of books and seen movies about how amazing the first kiss with the one could be. He’s heard it described from fireworks to electricity. He didn’t expect them all to be right.

+

Connor Walsh may be smart, clever, and extremely pretty--- a man whose heart he tried to protect from ever being broken--- but he has found out that he’s no match for Oliver Hampton who is incredibly smart, undeniably handsome, and has a heart of gold.

In the face of toothy smiles, thick-rimmed glasses, dorky laughs, lame musicals, and pineapple pizza, it was Connor who never stood a chance. He thinks he was doomed to fall in love with Oliver from the very start. He wouldn’t have it any other way.

**Notes for the Chapter:**

> it's done guys! I would really like to personally thank everyone who has stuck with this from my 11 month disappearance to the ever changing chapter number count. thank you so much! i know i don't reply to comments on here but that doesn't mean i dont squeal like an idiot every time i read ur reviews. it's really what has kept me going. Your comments/kudos/private messages is just the best kind of support so really thank you to all
> 
> it's been a ride folks i hope i didnt disappoint too horribly!
> 
> au revoir!

**Author's Note:**

> find me @ clarisselaruethless.tumblr.com


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